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Holiday houses in Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
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Guest favourite
Rental unit in Logan Square
4.91 out of 5 average rating, 264 reviewsBright & Lofty Bucktown 1br
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NzU1MzQxODY1MjQ3OTU2NDIx/original/5988b892-d6c4-4657-9caa-e39ca50e2821.jpeg?im_w=720)
Guest favourite
Rental unit in Forest Park
4.99 out of 5 average rating, 102 reviewsSunny 1 bedroom apartment 1 block from restaurants
![](https://a0.muscache.com/im/pictures/8d04133b-a607-4a9c-962e-6b630bb541e2.jpg?im_w=720)
Guest favourite
Guesthouse in Lincoln Square
4.88 out of 5 average rating, 234 reviewsPrivate Coach house near Lincoln Square!
![](https://a0.muscache.com/im/pictures/5c568f1c-240f-4df6-99cb-16393616359d.jpg?im_w=720)
Guest favourite
Rental unit in Avondale
4.97 out of 5 average rating, 127 reviewsDesigner Avondale Attic
![](https://a0.muscache.com/im/pictures/755e2d4d-1c3c-493c-8871-2c25259af389.jpg?im_w=720)
Guest favourite
Rental unit in Lincoln Park
4.98 out of 5 average rating, 308 reviewsRedesigned Lower Level Studio in Historic Building
![](https://a0.muscache.com/im/pictures/b002b25c-296d-4dd6-b128-482c3272f9a2.jpg?im_w=720)
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 116 reviewsGorgeous Studio 15 Minutes From Ohare!
![](https://a0.muscache.com/im/pictures/3b866b24-d817-428c-8b01-4641152b22b1.jpg?im_w=720)
Guest favourite
Guest suite in Andersonville
4.96 out of 5 average rating, 327 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
![](https://a0.muscache.com/im/pictures/miso/Hosting-46510058/original/e87a2d41-dca8-45fe-b064-33b85f2ff567.jpeg?im_w=720)
Guest favourite
Rental unit in Gold Coast
4.88 out of 5 average rating, 147 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Quick stats about holiday rentals in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Schaumburg Holiday rentals
- Rentals with an accessible height bed Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Kid-friendly rentals Chicago
- Bed and breakfasts Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- Apartment rentals Chicago
- Townhouse rentals Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
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- Monthly Rentals Chicago
- Rentals with lake access Chicago
- House rentals Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Fitness-friendly rentals Chicago
- Mansion rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with beach access Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
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