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
Guesthouse in Little Italy
4.99 out of 5 average rating, 792 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 240 reviewsStylish Studio in Historic Logan Square
Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 304 reviewsRedesigned Lower Level Studio in Historic Building
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 362 reviewsContemporary, private suite w fireplace
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 570 reviewsGreat Location! Gold Coast! 07
Guest favourite
Guest suite in North Center
4.96 out of 5 average rating, 107 reviewsModern Garden Apartment in Lincoln Square
Guest favourite
Guest suite in Logan Square
4.97 out of 5 average rating, 230 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Guest favourite
Home in Chicago
4.98 out of 5 average rating, 208 reviewsWrigleyville Southport Studio
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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