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.
Holiday rentals for every style
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Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
25 Oct – 1 Nov
Apartment in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
10 – 17 Jan
Apartment in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
24 Sept – 1 Oct
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
22 – 29 Oct
Apartment in Chicago
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
10 – 17 Jan
Loft in Forest Park
4.96 out of 5 average rating, 463 reviewsWalk to Oak Park from a Bright Madison Street Loft
9 – 16 Dec
Apartment in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
23 – 30 Sept
Apartment in Chicago
4.96 out of 5 average rating, 322 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
6 – 13 Dec
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
- New Buffalo Holiday rentals
- Bed and breakfasts Chicago
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- Rentals with pools Chicago
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- Monthly Rentals Chicago
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- Hotel rentals Chicago
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