Chicago, IL Vacation Rentals

Explore 206 vacation rentals, homes, and villas in Chicago, IL for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Fitness Center and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $63 per night and featuring up to 9 bedrooms and 7 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

206 Vacation Rentals in Chicago

Plymouth Collection: 2BD High Floor w/ Gym,Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 25 - 27
$536 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 10th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 21 - 23
$254 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay now! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than the current photos. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 18 - 20
$475 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers. This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 19 - 21
$538 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. All the bedrooms feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Parking We include parking for one vehicle in the lot directly across the street at no additional charge! Any additional vehicles will receive a discounted rate. *Please note that this unit is currently undergoing a full repaint. As a result, wall colors and decor may vary slightly from what is shown in the photos. However, the layout and bed sizes will remain exactly the same. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 27 - 29
$293 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish place blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all Chicago attractions, it’s an ideal home base for business travelers and city explorers alike. This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen This unit is designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both, one double sized bed and one king sized bed designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 12 - 14
$453 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: Top Floor with Gym & Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 26 - 28
$309 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 11th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym! This newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away! Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 17 - 19
$902 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay now! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. *Please note that this unit is currently undergoing a full repaint. As a result, wall colors and decor may vary slightly from what is shown in the photos. However, the layout and bed sizes will remain exactly the same. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 25 - 27
$544 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers. This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: Top Floor w/ Rooftop & Lobby

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 17 - 19
$848 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment located on the 11th floor features a full kitchen, in-unit laundry, and comfortable living spaces, . Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay today! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Two bedrooms feature a king sized bed and the other two bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Oct 5 - 7
$129 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers. This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 11 - 13
$735 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king and the other feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 25 - 27
$484 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 9th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 11 - 13
$734 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 11 - 13
$699 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 4BD 3BA High Floor with Gym

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 23 - 25
$433 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment located on the 10th floor features a full kitchen, in-unit laundry, and comfortable living spaces, . Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay today! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king sized bed while the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA High Floor with Gym

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 17 - 19
$523 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy top floor living as this unit sits on the 10th level. The building also features a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 17 - 19
$299 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers. This newly renovated plcae is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 18 - 20
$883 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay now! This newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Parking We include parking for one vehicle in the lot directly across the street at no additional charge! Any additional vehicles will receive a discounted rate. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, IL, US
2 Bedrooms 4 Guests
Sep 17 - 19
$334 night

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers. This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, IL, US
4 Bedrooms 8 Guests
Sep 18 - 20
$1,016 night

Discover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment located on the 9th floor features a full kitchen, in-unit laundry, and comfortable living spaces. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it’s the perfect base for exploring Chicago. Book your stay today! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedrooms feature a king sized bed while the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than the current photos. Amenties Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 10:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 24 - 26
$450 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

DO NOT BOOK-TESTING

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 11 - 13
$699 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, IL, US
3 Bedrooms 6 Guests
Sep 11 - 13
$661 night

Welcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy top floor living as this unit sits on the 9th level. The building also features a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play! This newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away. Living Room & Kitchen Designed for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago. Bedroom & Bathroom The sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. Amenities Guests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. Guests will have access to the entire unit as well as all common areas. For guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. Getting around is effortless with several CTA train stations and bus routes just steps away, providing quick access throughout the city. Millennium Park, Buckingham Fountain, Navy Pier, the Magnificent Mile, Soldier Field, and Museum Campus are all within a 5–15 minute drive or transit ride. Midway International Airport is approximately 20–25 minutes away by car, while O’Hare International Airport is about 30–40 minutes away, making travel convenient for every guest. Check-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we’ll do our best to accommodate your request. No Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop. Pet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy. Quiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment. Rooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space. Maximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted. Security: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. Heating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests. Please note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. License Number: 3069885 License number: 3069885

Vacation Rentals in Chicago by Amenities & Features

Get to Know Chicago

Chicago, Illinois, is a vibrant city that boasts a rich mix of cultural, culinary, and architectural delights. The city's skyline is a testament to its architectural prowess with iconic structures like the Willis Tower and the John Hancock Center. An architectural river cruise offers stunning views of these buildings and provides insights into their history. The city's cultural scene is vibrant and diverse. The Art Institute of Chicago houses an impressive collection of artworks from around the world, while the Field Museum showcases natural history exhibits. For music lovers, Chicago's blues and jazz scenes are legendary. Chicago also has a strong sports culture with teams in all major sports leagues. Catching a game at Wrigley Field or Soldier Field can be an exciting experience. For nature enthusiasts, the city offers plenty of green spaces. Millennium Park, home to the famous Cloud Gate sculpture (also known as "The Bean"), and Grant Park are perfect for leisurely strolls or picnics. Foodies will find much to love in Chicago's culinary scene. The city is famous for its deep-dish pizza and Chicago-style hot dogs. A visit to Navy Pier or one of the city's food festivals can be a gastronomic delight. Finally, Chicago is known for its shopping experiences. From luxury boutiques on Magnificent Mile to unique shops in neighborhoods like Wicker Park and Andersonville, there's something for every shopper. In essence, Chicago offers a diverse range of experiences that cater to all types of travelers. Its rich history, vibrant culture, stunning architecture, delicious food scene make it a destination worth exploring.
Chicago, Illinois is known for its humid continental climate, which brings about four distinct seasons. During the summer months of June to August, the city typically experiences average high temperatures in the 80s Fahrenheit. However, during heat waves, it's not uncommon for temperatures to reach into the 90s. These months also bring about the highest levels of humidity and rainfall, along with occasional thunderstorms. Despite these conditions, summer remains a popular time for visitors due to the numerous outdoor festivals and events. The winter months from December to February can be quite cold with high temperatures often below freezing. However, it's also common to experience highs in the 30s and 40s Fahrenheit during this season. Snowfall is a regular occurrence and can sometimes be heavy. Even with chilly weather conditions, winter in Chicago offers its own charm with holiday decorations and ice skating opportunities. Spring from March to May and fall from September to November serve as transitional seasons with milder temperatures. Spring sees temperatures ranging from the 40s to 70s Fahrenheit while fall offers cooler temperatures in the 50s and 60s along with beautiful autumn foliage. The most popular time to visit Chicago is during late spring through early fall when weather conditions are most pleasant for outdoor activities such as sightseeing or attending one of many city festivals. Each season however offers its own unique appeal depending on your interests.
Chicago, Illinois, is a vibrant cultural center offering a plethora of activities for those interested in arts, history, and local traditions. The city's art scene is eclectic and lively, boasting numerous museums and galleries. The Art Institute of Chicago is home to one of the world's largest collections of Impressionist and Post-Impressionist art. For fans of contemporary art, the Museum of Contemporary Art Chicago exhibits cutting-edge works from across the globe. History enthusiasts will value the rich history embodied in Chicago's architecture. The city is known for its architectural innovation with buildings designed by renowned architects like Frank Lloyd Wright and Louis Sullivan. Guided tours are available to explore these architectural wonders. The music scene in Chicago is equally noteworthy with deep roots in blues, jazz, gospel, hip hop, and house music. Establishments such as Buddy Guy's Legends and Kingston Mines host live blues shows while Green Mill Cocktail Lounge offers a genuine jazz experience. Local traditions can be explored through various neighborhood festivals that honor Chicago's varied cultural heritage. These include the Taste of Chicago food festival in Grant Park or neighborhood-specific events like Pilsen's Mole de Mayo or Andersonville's Midsommarfest. Lastly, strolling around Chicago is an enjoyable experience itself with its lakefront trails providing breathtaking views of Lake Michigan and downtown skyline. However, for longer distances or when time constraints exist, public transportation including buses and 'L' trains offer efficient service throughout the city.
Chicago, Illinois is a city that is rich in activities and attractions for children. The Museum of Science and Industry, with its interactive exhibits that span from space exploration to natural disasters, is a popular destination for families. Children can experience stepping inside a real U-505 submarine or taking a ride on the Pioneer Zephyr, the first diesel-electric streamlined train. The Navy Pier is another family-friendly location. It houses the Chicago Children's Museum where kids can climb through a multi-story schooner or engage their creativity in the Maker Lab. The Pier also features an iconic Ferris wheel that provides breathtaking views of the city and Lake Michigan. Animal enthusiasts will enjoy the Lincoln Park Zoo, one of North America's oldest zoos. It's free to the public and houses over 1,000 animals from around the globe. Interactive exhibits like Farm-in-the-Zoo offer children an up-close encounter with farm animals. The Shedd Aquarium offers another opportunity for wildlife encounters. Here, children can see creatures ranging from beluga whales to sea otters and even have tactile experiences with stingrays in the Stingray Touch exhibit. For outdoor activities, Millennium Park provides ample space for kids to expend energy. They'll enjoy cooling off in Crown Fountain during summer or ice skating at McCormick Tribune Ice Rink in winter. Lastly, enrich your child's experience by catching a show at Chicago Children's Theatre or exploring outer space at Adler Planetarium. In summary, Chicago offers an array of family-friendly activities that are not only entertaining but also educational. From diverse museums and parks to entertainment venues and educational experiences - there are endless opportunities for fun-filled family adventures.
Chicago, Illinois, while known as a thriving city, is also a haven for nature lovers with its numerous parks and outdoor activities. The city boasts over 570 parks, including the vast Lincoln Park which offers a free zoo, conservatory, and various trails. Bird watchers and botany enthusiasts will find the Alfred Caldwell Lily Pool within this park to be a delightful surprise. The Chicago Botanic Garden is another destination that nature enthusiasts should not miss. It covers 385 acres and includes 27 gardens and four natural areas. This place is not just for relaxation but also provides opportunities for bird watching and learning about diverse plant species. Lake Michigan presents plenty of water-based activities. Visitors can swim at one of the many beaches or engage in boating or paddleboarding. The lakefront trail that runs parallel to Lake Michigan is ideal for biking or walking while taking in the picturesque views. The North Park Village Nature Center is another attraction for outdoor lovers with its trails meandering through woodland, wetland, prairie and savanna - perfect for hiking within the city's boundaries. Additionally, the Chicago River offers architectural boat tours where visitors can learn about the city's history while being outdoors. Kayaking on the river becomes a favorite activity during warmer months. Just beyond Chicago's borders are Indiana Dunes National Park and Starved Rock State Park which provide hiking trails with breathtaking views as well as camping facilities. In summary, despite its urban setting, Chicago has an abundance of offerings for those who enjoy connecting with nature - from parks teeming with flora and fauna to water-based activities on Lake Michigan.
Visitors traveling to Chicago, Illinois, have a multitude of transportation choices. The majority of tourists reach the city by air, landing at either O'Hare International Airport or Midway International Airport, both of which offer a wide range of domestic and international flights. Alternatively, Amtrak provides rail service to Chicago Union Station from different regions across the country for those who favor land travel. Upon arrival in the city, there are numerous ways to navigate around. The Chicago Transit Authority (CTA) runs a comprehensive network of buses and trains that service the city and many surrounding suburbs. The 'L' train system is especially handy for traversing downtown and accessing popular sites such as Navy Pier, Millennium Park, and Wrigley Field. Taxis and ride-sharing services like Uber and Lyft are easily accessible throughout the city. For those who prefer self-driving, car rental services are available at both airports as well as various locations within the city. Chicago is also accommodating to cyclists with its Divvy bike-sharing program offering thousands of bikes at hundreds of stations across the city. This can be an enjoyable way to discover neighborhoods like Lincoln Park or Lakeview. In terms of walkability, much of Chicago is pedestrian-friendly. Downtown areas such as The Loop are easy to navigate on foot with many attractions within walking distance from each other. However, due to the vast size of the city and some attractions being spread out, using public transportation or a car may be necessary for more extensive exploration. To sum up, whether you're flying or taking a train into Chicago; whether you prefer bus rides, train rides, taxis or biking; Chicago caters to every traveler's needs with its diverse range of transportation options.

Chicago FAQs

Chicago offers a plethora of activities for all types of travelers. You can explore the Art Institute of Chicago, take an architecture river cruise, visit Millennium Park and see the famous 'Bean' sculpture, shop on the Magnificent Mile, enjoy views from the Willis Tower Skydeck, and indulge in Chicago's famous deep-dish pizza. Don't forget to catch a show at the Chicago Theatre or a baseball game at Wrigley Field!
The best time to visit Chicago is during the spring (April to June) and fall (September to October) when the temperatures are mild, and the city hosts numerous festivals. Summers can be hot and crowded, but they are also vibrant with lake activities and outdoor events. Winters are cold and snowy, offering a different charm with holiday lights and ice skating.
Chicago has an extensive public transportation system called the 'L' (short for 'elevated train') that is efficient and affordable. Buses also cover the city extensively. For more convenience, you can use taxis or rideshare services like Uber and Lyft. The city is also very bike-friendly, with numerous bike rental stations and dedicated lanes.
Chicago is known for its diverse culinary scene. For a taste of the city's iconic deep-dish pizza, visit Lou Malnati's or Giordano's. For upscale dining, Alinea is a renowned choice. Other must-tries include Portillo's for Chicago-style hot dogs, Garrett Popcorn Shops for gourmet popcorn, and any of the city's many steakhouses. Don't miss the diverse offerings in neighborhoods like Chinatown, Little Italy, and Pilsen.
Chicago is a city of neighborhoods, each with its own character. The Loop is the central business district with iconic buildings and theaters. River North is known for its art galleries and nightlife. Wicker Park and Logan Square are hipster havens with cool cafes and vintage shops. Lincoln Park is great for families with its namesake park and zoo. And don't miss the historic architecture and Mexican culture in Pilsen.
Yes, there are several great day trips from Chicago. You can visit the charming college town of Evanston, explore the Illinois Railway Museum in Union, or take a hike in Starved Rock State Park. For a more urban escape, consider Milwaukee in neighboring Wisconsin, or head to the Indiana Dunes on the shores of Lake Michigan for some beach time.

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Vacation Rentals Near Chicago

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