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
Guest suite in Chicago
4.98 out of 5 average rating, 110 reviewsGorgeous Studio 15 Minutes From Ohare!
Mar. 24 – 31
$169 CAD per night
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 105 reviewsHumboldt Park Loft
Sep. 4 – 11
$226 CAD per night
Guest favourite
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
Sep. 4 – 11
$161 CAD per night
Guest favourite
Apartment in Chicago
4.91 out of 5 average rating, 370 reviewsThe Grotto of Logan Square
Sep. 9 – 14
$231 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
Oct. 3 – 10
$206 CAD per night
Guest favourite
Apartment in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
Sep. 10 – 17
$178 CAD per night
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
Mar. 30 – Apr. 6
$222 CAD per night
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Mar. 28 – Apr. 4
$200 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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