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
Guesthouse in Chicago
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Oct. 15 – 22
Apartment in Cicero
4.98 out of 5 average rating, 203 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Apr. 25 – May 2
Home in Chicago
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
Feb. 19 – 26
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec. 10 – 17
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Dec. 31 – Jan. 7
Guesthouse in Chicago
4.99 out of 5 average rating, 786 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Nov. 16 – 23
Home in Chicago
4.95 out of 5 average rating, 122 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Dec. 19 – 26
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
Jul. 20 – 27
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
- Downtown Chicago Vacation rentals
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- Hotel rentals Chicago
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