Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Oct. 25 – Nov. 1
Apartment in Lincoln Park
4.83 out of 5 average rating, 208 reviewsCozy Lincoln Park Studio - Steps to Zoo!
Jan. 10 – 17
Apartment in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
Sep. 24 – Oct. 1
Guest suite in Chicago
4.91 out of 5 average rating, 358 reviewsContemporary, private suite w fireplace
Oct. 22 – 29
Apartment in Chicago
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
Jan. 10 – 17
Loft in Forest Park
4.96 out of 5 average rating, 463 reviewsWalk to Oak Park from a Bright Madison Street Loft
Dec. 9 – 16
Apartment in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Sep. 23 – 30
Apartment in Chicago
4.96 out of 5 average rating, 322 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec. 6 – 13
Quick stats about vacation 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 Vacation rentals
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- Bed and breakfasts Chicago
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