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, 703 reviewsGreat location. Free parking.
Jul. 21 – 26
$192 CAD per night
Guest favourite
Guest suite in Chicago
4.96 out of 5 average rating, 320 reviewsGorgeous, cozy 1-bedroom Suite in Andersonville
Feb. 28 – Mar. 7
$150 CAD per night
Guest favourite
Home in Roscoe Village
4.94 out of 5 average rating, 209 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
Jan. 8 – 15
$218 CAD per night
Guest favourite
Apartment in Lincoln Square
4.96 out of 5 average rating, 322 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec. 10 – 17
$234 CAD per night
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
Feb. 27 – Mar. 6
$248 CAD per night
Guest favourite
Apartment in Logan Square
4.91 out of 5 average rating, 371 reviewsThe Grotto of Logan Square
Oct. 1 – 6
$229 CAD per night
Guest favourite
Apartment in Chicago
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
Sep. 13 – 20
$178 CAD per night
Guest favourite
Loft in Forest Park
4.96 out of 5 average rating, 463 reviewsWalk to Oak Park from a Bright Madison Street Loft
Dec. 9 – 16
$207 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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