Holiday houses in Chicago
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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
Guest favourite
Rental unit in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Guest favourite
Guesthouse in Lincoln Square
4.88 out of 5 average rating, 235 reviewsPrivate Coach house near Lincoln Square!
Guest favourite
Rental unit in West Loop
4.87 out of 5 average rating, 222 reviewsGarden Apartment in the Historic Heart of the City
Guest favourite
Guest suite in Andersonville
4.96 out of 5 average rating, 327 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Guest favourite
Guest suite in North Center
4.96 out of 5 average rating, 108 reviewsModern Garden Apartment in Lincoln Square
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 117 reviewsGorgeous Studio 15 Minutes From Ohare!
Guest favourite
Rental unit in Avondale
4.97 out of 5 average rating, 127 reviewsDesigner Avondale Attic
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 427 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Quick stats about accommodation 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 Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- Schaumburg Accommodation & holiday rentals
- Private suite rentals Chicago
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- Lakehouse rentals Chicago
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