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.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chicago vacation rentals
Other great vacation rentals in Chicago
Guest favourite
Home in Chicago
4.9 out of 5 average rating, 334 reviewsPrivate 3rd Floor Apartment
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 112 reviewsGorgeous Studio 15 Minutes From Ohare!
Guest favourite
Apartment in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest favourite
Guesthouse in Andersonville
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Guest favourite
Apartment in Logan Square
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Guest favourite
Guest suite in Chicago
4.95 out of 5 average rating, 243 reviewsGreat location, private entry and patio!
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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