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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
![](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/miso/Hosting-40631718/original/82a62e45-8126-4815-83a5-b682ae520690.jpeg?im_w=720)
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 436 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
![](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
![](https://a0.muscache.com/im/pictures/miso/Hosting-946948795869099240/original/09e5af13-8bde-4a3d-adb6-d272cacf02f9.jpeg?im_w=720)
Guest favourite
Rental unit in Andersonville
4.98 out of 5 average rating, 41 reviewsModern Vintage Walkable to Dining & Lakeshore
![](https://a0.muscache.com/im/pictures/d154c73e-523e-4680-a1d0-d5a939128b0c.jpg?im_w=720)
Guest favourite
Guest suite in West Loop
4.91 out of 5 average rating, 92 reviewsCozy one-bedroom suite in the heart of West Loop
![](https://a0.muscache.com/im/pictures/airflow/Hosting-849968138671103633/original/829f7b74-5b22-464b-b550-43209eb8a0ac.jpg?im_w=720)
Guest favourite
Rental unit in Logan Square
4.95 out of 5 average rating, 42 reviewsAffordable, Cool Artist Studio
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6Mzk3OTMyMA%3D%3D/original/86b2aa3f-2ac7-4d59-8088-5692fe4b0140.jpeg?im_w=720)
Guest favourite
Rental unit in Uptown
5 out of 5 average rating, 7 reviews2 Room Apartment in Vintage Bldg
Quick stats about holiday rentals in Chicago
Total rentals
10T properties
Total number of reviews
5L reviews
Family-friendly rentals
4.8T properties are a good fit for families
Pet-friendly rentals
3.3T properties allow pets
Rentals with a pool
1.1T properties have a pool
Rentals with dedicated workspaces
6.6T 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
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Rentals with a patio Chicago
- Rentals with a sauna Chicago
- Family-friendly rentals Chicago
- Smoking-friendly rentals Chicago
- Family-friendly rentals Chicago
- Beachfront rentals Chicago
- Rentals with a balcony Chicago
- Mansion rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- House rentals Chicago
- Private suite rentals Chicago
- Rentals with beach access Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Waterfront rentals Chicago
- Rentals with pools Chicago
- Rentals with an accessible-height bed Chicago
- Monthly Rentals Chicago
- Boutique hotel rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a fireplace Chicago
- Flat rentals Chicago
- Loft rentals Chicago
- Townhouse rentals Chicago
- Lakehouse rentals Chicago
- Bed and breakfasts Chicago
- Yurt Rentals United States
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- Holiday Cottages United Kingdom
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