Chicago, Illinois Vacation Rentals

Explore 115 rental homes and villas in Chicago, Illinois for your next vacation or business travel. With private vacation home rentals, enjoy a more personalized stay and a wide range of amenities such as Air Condition Homes, Pet-Friendly Homes and Best Affordable Homes. With a wide range of homes to offer, pricing can start as low as $82 per night with homes containing as many as 9 bedrooms and 7 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

Types of vacation rentals in Chicago

Where to stay in Chicago

Show all homes

Booking a vacation rental in Chicago, Illinois?

Here are some things to know to support your visit:

Chicago Overview
Immerse yourself in the heart of the Midwest by exploring the dynamic cityscape of Chicago, Illinois. This bustling metropolis is not only a hub of architectural marvels but also a sanctuary for cultural aficionados, food enthusiasts, and nature lovers alike. Begin your journey by marveling at the towering skyline, punctuated by the awe-inspiring Willis Tower and the sleek contours of the John Hancock Center. To truly appreciate these feats of engineering, embark on an architectural river cruise that weaves through the city, offering unparalleled views and fascinating narratives of Chicago's storied buildings. Art and history converge at the Art Institute of Chicago, where you can wander through galleries filled with world-renowned masterpieces. Meanwhile, the Field Museum invites you to step back in time with its extensive natural history exhibits. For those with a penchant for music, the soulful melodies of Chicago's blues and jazz clubs are an absolute must, echoing the city's deep-rooted musical heritage. Sports enthusiasts will revel in the electric atmosphere of Wrigley Field and Soldier Field, where the city's beloved teams play against a backdrop of passionate fans. And for a serene escape, meander through the lush landscapes of Millennium Park, where the iconic Cloud Gate sculpture reflects the city's skyline, or unwind in the sprawling expanse of Grant Park. Chicago's gastronomic offerings are as diverse as its neighborhoods. Indulge in the city's signature deep-dish pizza, savor a Chicago-style hot dog, or explore the culinary delights at Navy Pier. The city's food festivals are a celebration of flavors that tantalize the taste buds of even the most discerning gourmets. Enhance your stay by renting a private home, where you can enjoy the luxury of your own space, many of which are pet-friendly, allowing you to bring along your furry companions. Select homes boast swimming pools, offering a refreshing respite from the city's buzz. For those drawn to the water, Chicago's beaches along Lake Michigan provide a picturesque setting for relaxation and recreation, with the city's impressive skyline as your backdrop. Shopping in Chicago is an adventure in itself, with the Magnificent Mile offering high-end retail therapy and neighborhoods like Wicker Park and Andersonville featuring unique boutiques and artisanal finds. Chicago's tapestry of experiences ensures that every visitor leaves with cherished memories. From its towering skyscrapers to its vibrant waterfront, this city is a treasure trove of discoveries waiting to be made.
Cultural Attractions in Chicago
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.
Kids IconFamily friendly activities in Chicago
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.
Nature IconOutdoor activities in Chicago
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.
Weather IconWeather in Chicago
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.
Transportation in Chicago
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.