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
Vacation Rentals in Chicago by Amenities & Features
Get to Know Chicago
Chicago OverviewChicago, 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 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.
Weather in ChicagoChicago, 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 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.
Cultural Attractions in ChicagoChicago, 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 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.
Family friendly activities in ChicagoChicago, 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 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.
Outdoor activities in ChicagoChicago, 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.
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.
Transportation in ChicagoVisitors 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.
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
What is there to do in Chicago?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!
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!
When is the best time to visit Chicago?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.
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.
How do I get around in Chicago?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 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.
What are some good places to eat in Chicago?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 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.
What are the best neighborhoods to explore in Chicago?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.
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.
Are there any day trips from Chicago?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.
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.
More space, more privacy, more points with every home rental.
What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.























