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
Apartment in Chicago
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Oct. 21 – 28
Guest suite in Chicago
4.98 out of 5 average rating, 111 reviewsGorgeous Studio 15 Minutes From Ohare!
Apr. 22 – 29
Guest suite in Andersonville
4.96 out of 5 average rating, 320 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Jan. 6 – 13
Apartment in Chicago
4.91 out of 5 average rating, 372 reviewsThe Grotto of Logan Square
Sep. 3 – 8
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
Home in Berwyn
4.92 out of 5 average rating, 240 reviewsPrivate apartment with retro vibe
Aug. 28 – Sep. 4
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, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Nov. 12 – 19
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
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