Save up to 46%
9,300 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 54%.
Find your perfect vacation rental in Chicago: from $33 per night
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Chicago is a wonderful vacation spot if you want an accommodation with a pool, as 25% 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. two-thirds 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 July (7/26 – 8/2). During this week, a night will cost on average $733. Prices decrease in a week of January (1/4 – 1/11), where average prices are $336.
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 August (8/9 – 8/16). Only 7% of the rentals are still available. On the other hand, the week with the most available offers is in October (10/26 – 11/2).
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 | 9,248 rentals |
|---|---|
| 💳 Possible discounts | up to 65% |
| 🌙 Nightly prices starting at | $33 |
| ⭐ Popular amenities | Internet, Pool and Kitchen |
| 🐾 Pet friendly homes | 4,248 homes |
| 🏊 Vacation rentals with pools | 2,335 homes |
At the moment, there are 9,248 vacation homes from 21 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 46% 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.