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
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
Oct. 15 – 22
$253 CAD per night
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec. 10 – 17
$229 CAD per night
Guest favourite
Guesthouse in Chicago
4.95 out of 5 average rating, 367 reviewsCozy Coach House
Aug. 19 – 26
$197 CAD per night
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 322 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Jan. 17 – 24
$149 CAD per night
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 226 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Oct. 1 – 8
$204 CAD per night
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Oct. 15 – 22
$192 CAD per night
Guest favourite
Guesthouse in Chicago
4.91 out of 5 average rating, 342 reviewsPrivate, Charming, Coach House Loft in Andersonville
Dec. 8 – 15
$274 CAD per night
Guest favourite
Cabin in Griffith
4.91 out of 5 average rating, 158 reviewsBeautiful Rustic Cabin for Two!
Nov. 5 – 12
$130 CAD per night
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
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