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
Condo in Chicago
4.97 out of 5 average rating, 332 reviewsLincoln Square Gem!
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 120 reviewsDesigner Avondale Attic
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Guest favourite
Apartment in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Guest favourite
Guesthouse in Edgewater
4.95 out of 5 average rating, 368 reviewsCozy Coach House
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
Guest suite in Chicago
4.98 out of 5 average rating, 112 reviewsGorgeous Studio 15 Minutes From Ohare!
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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