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
Superhost
Apartment in Chicago
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Feb. 17 – 24
$210 CAD per night
Guest favourite
Guesthouse in Chicago
4.88 out of 5 average rating, 106 reviewsThe Roscoe Village Guesthouse
Jan. 26 – Feb. 2
$201 CAD per night
Guest favourite
Cabin in Griffith
4.91 out of 5 average rating, 154 reviewsBeautiful Rustic Cabin for Two!
Jan. 8 – 15
$133 CAD per night
Guest favourite
Guesthouse in Chicago
4.99 out of 5 average rating, 782 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Oct. 25 – Nov. 1
$249 CAD per night
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 103 reviewsComfortable, modern apartment 20 Min from Downtown
Nov. 4 – 11
$213 CAD per night
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 224 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
Aug. 31 – Sep. 7
$209 CAD per night
Guest favourite
Guesthouse in Chicago
4.95 out of 5 average rating, 366 reviewsCozy Coach House
Aug. 19 – 26
$199 CAD per night
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 192 reviewsCozy Urban Garden Apartment
Apr. 22 – 29
$141 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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