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
Apartment in Chicago
4.82 out of 5 average rating, 443 reviewsLovely Andersonville Apt with Ideal Location
Guest favourite
Guest suite in Chicago
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest favourite
Guest suite in East Rogers Park
4.96 out of 5 average rating, 104 reviews1BR Historic Rogers Park/West Ridge unit- Sleeps 4
Guest favourite
Guest suite in Lincoln Square
4.97 out of 5 average rating, 371 reviewsPrivate suite in Lincoln Square
Guest favourite
Apartment in Lincoln Park
4.98 out of 5 average rating, 307 reviewsRedesigned Lower Level Studio in Historic Building
Guest favourite
Apartment in Cicero
4.98 out of 5 average rating, 214 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Guest favourite
Guest suite in Lake View
4.95 out of 5 average rating, 179 reviews1 mile from Wrigley Field
Guest favourite
Apartment in Avondale
4.97 out of 5 average rating, 124 reviewsDesigner Avondale Attic
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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- Private suite rentals Chicago
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