Find your perfect vacation rental in Chicago from just $24 per night!
Save up to 74%
11,066 beautiful vacation rentals from 19 vacation rental websites, including Booking.com and HomeToGo, are available in Chicago. Using HomeToGo you can directly search and compare the prices of each listed property to find the best deal and save up to 64%.
Find Fantastic yet Inexpensive Rentals
Book Vacation Rentals with the Highest User Rating
Choose local, trusted payment methods, plus trip insurance and add-on services.
Experience seamless, hands-on support for any booking questions or concerns.
Trust in the quality and comfort of your stay with verified guest reviews.
Spend your budget exactly as planned by comparing thousands of providers.
Transform vacation planning into a joy with advanced, AI-powered search tools.
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Chicago is a wonderful vacation spot if you want an accommodation with a pool, as 23% of the vacation rentals there have one. Interestingly, our data shows that more hotel room have a pool than apartment rental. Additionally, they can welcome 8 vacationers, on average, while apartment rental with pools can host an average of 3 people. many of Chicago's vacation homes including a pool are located within two kilometres of water, choose between some pool time or waterfront moments.
We analyzed vacation homes, cottages and apartments to display a price graph showing the average price per night in Chicago. The week with the highest average prices is in October (10/4 – 10/11). During this week, a night will cost on average $1,072. Prices decrease in a week of December (12/13 – 12/20), where average prices are $189.
Have a look at the above graph to see the global availability of vacation rentals in Chicago. The week with the highest booking rate is in November (11/15 – 11/22). Only 8% of the rentals are still available. On the other hand, the week with the most available offers is in March (3/1 – 3/8).
There's no shortage of options to entertain your family if you're visiting Chicago with kids who love animals. Shedd Aquarium is both exciting and educational for kids, with fun interactive displays, live shows, play zones, and exhibits on marine life around the world. Brookfield Zoo is a vast, 216-acre nature park in Chicagoland that's home to hundreds of different animals, a fun motor safari tram, a huge butterfly world, and the Family Play Zoo where you can dress up as zookeepers or furry friends. Closer to downtown, historic Lincoln Park Zoo has exotic creatures like red pandas, snow monkeys, leopards, a classic carousel, and other fun rides.
A ride for kids of all ages is the Navy Pier's Centennial Wheel, which gives fantastic city views topped only by heading up to 360 Chicago on the 94th floor of the John Hancock Tower on Michigan Avenue. For a different perspective of Chicago, hop on board the Tall Ship Windy at Navy Pier and enjoy great city views from Lake Michigan aboard an authentic 4-mast schooner. Kids can even join in and hoist the sails themselves!
The world-class Chicago Children's Museum has hands-on, interactive displays and exhibits, including the popular ""Dinosaur Expedition"" where kids can join an archaeological dig and explore a real fossil pit. The Adler Planetarium lets kids have the feeling of going to outer space without even leaving Chicago, and LEGOLAND Chicago is a toy wonderland with life-sized LEGO displays, interactive areas, and a 4D theatre.
Art and history enthusiasts will have plenty of choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and more. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.
For improvisational comedy and performance art, catch a show at The Annoyance Theater, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theater awaits.
The city's most popular attraction is the Lincoln Park Zoo, which houses African apes and other interesting species. Trivia lovers will be impressed to learn that Chicago is home to three out of America's five tallest buildings: the Sears Tower, Trump Tower, and the Aon Center.
Chicago's international neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.
What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Center for stunning views of the city and over Lake Michigan.
At this interactive museum you'll find a life-size replica coal mine and recreated historic Chicago streets with functional shops.
One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape.
This urban park in the center of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs, and fun events are held regularly at the park.
As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, ancient sculptures, and more feature.
| 🏡 Vacation rentals available | 11,066 rentals |
|---|---|
| 💳 Possible discounts | up to 64% |
| 🌙 Nightly prices starting at | $24 |
| ⭐ Popular amenities | Internet, Pool and Kitchen |
| 🐾 Pet friendly homes | 4,679 homes |
| 🏊 Vacation rentals with pools | 2,505 homes |
At the moment, there are 11,066 vacation homes from 19 different providers in Chicago.
Many travellers are searching for Internet, Pool, and Kitchen when booking a vacation home in Chicago.
If you're travelling with a dog, over 42% of vacation rentals in Chicago are pet-friendly.
When booking a vacation rental in Chicago, remember that the rainiest months are usually March and April, with February often being the sunniest.