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Holiday rentals 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 Near North Side
4.89 out of 5 average rating, 390 reviewsGreat Location Studio in the Gold Coast!!
![](https://a0.muscache.com/im/pictures/miso/Hosting-3267902/original/d39e5e6b-311d-4a80-9804-714870ed8046.jpeg?im_w=720)
Guest favourite
Rental unit in Edgewater
4.93 out of 5 average rating, 391 reviewsRavenswood Guest House Annex
![](https://a0.muscache.com/im/pictures/d9783074-183f-4972-a6fe-2b14afc137ea.jpg?im_w=720)
Guest favourite
Rental unit in Wicker Park
4.96 out of 5 average rating, 101 reviewsSpacious Studio w/Balcony in Bucktown/Wicker Park
![](https://a0.muscache.com/im/pictures/miso/Hosting-958176890537691747/original/9263a134-cd15-48f9-a9c4-7ae123af8f54.jpeg?im_w=720)
Guest favourite
Apartment in Lake View
4.98 out of 5 average rating, 40 reviewsChic & Comfy • Close to Wrigley
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MzI4MjExMDc%3D/original/6e75e7a2-04ae-4e34-b4ee-be0c55345313.jpeg?im_w=720)
Guest favourite
Apartment in Lake View
4.89 out of 5 average rating, 9 reviewsCozy, sunny, boho condo in Uptown/Sheridan Park
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1118198200466838593/original/c0734f62-d9f8-43df-88ea-42703364f042.jpeg?im_w=720)
Guest favourite
Rental unit in Albany Park
5 out of 5 average rating, 11 reviewsBright Apartment
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Guest favourite
Rental unit in Uptown
5 out of 5 average rating, 13 reviewsIndustrial Designer Flat | Spacious 1BD 1BR *PETS*
![](https://a0.muscache.com/im/pictures/miso/Hosting-917294757690602460/original/b310ecc5-f2bc-4b5e-a77e-baa352b50d21.jpeg?im_w=720)
Guest favourite
Rental unit in Chicago
4.94 out of 5 average rating, 47 reviewsSerene Escape with King Sleep Number Bed, No Fees!
Quick stats about holiday rentals in Chicago
Total rentals
10K properties
Total number of reviews
497K reviews
Family-friendly rentals
4.8K properties are a good fit for families
Pet-friendly rentals
3.3K properties allow pets
Rentals with a pool
1.1K properties have a pool
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
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 a patio Chicago
- Beachfront rentals Chicago
- Rentals with pools Chicago
- Fitness-friendly rentals Chicago
- Rentals with an accessible-height bed Chicago
- Mansion rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Bed and breakfasts Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Family-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Flat rentals Chicago
- Private suite rentals Chicago
- Loft rentals Chicago
- House rentals Chicago
- Waterfront rentals Chicago
- Rentals with lake access Chicago
- Boutique hotel rentals Chicago
- Rentals with a sauna Chicago
- Lakehouse rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Rentals with a balcony Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Monthly Rentals Chicago
- Rentals with beach access Chicago
- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Townhouse rentals Chicago
- Smoking-friendly rentals Chicago
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