Apartment vacation rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Apartment rentals with air conditioning
Apartment in Chicago
4.92 out of 5 average rating, 329 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Chicago
4.95 out of 5 average rating, 256 reviewsHeart of Bucktown
Apartment in Logan Square
4.91 out of 5 average rating, 374 reviewsThe Grotto of Logan Square
Apartment in Chicago
4.89 out of 5 average rating, 474 reviewsiKlektik House Chicago / Robin
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Apartment in Chicago
4.81 out of 5 average rating, 371 reviewsWESTERN AVE ARTISTS LOFTS- Park Free
Apartment in Humboldt Park
4.98 out of 5 average rating, 109 reviewsHumboldt Park Loft
Apartment in Chicago
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Weekly apartment rentals
Apartment in Berwyn
4.87 out of 5 average rating, 141 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Apartment in Andersonville
4.98 out of 5 average rating, 253 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Chicago
4.96 out of 5 average rating, 112 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.98 out of 5 average rating, 172 reviewsBridgeport Garden Apartment
Apartment in Chicago
4.93 out of 5 average rating, 170 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Apartment in Chicago
4.8 out of 5 average rating, 385 reviews'Secret Garden' Apartment in Wrigleyville
Apartment in Chicago
4.88 out of 5 average rating, 191 reviewsComfort zone
Apartment in Chicago
4.9 out of 5 average rating, 343 reviewsSunny Logan Square Artists' home
Private apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 119 reviewsEdgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375
Apartment in Chicago
4.86 out of 5 average rating, 175 reviewsAttic apartment in a hip neighborhood!
Apartment in Wicker Park
4.96 out of 5 average rating, 249 reviewsNewly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Apartment in Chicago
4.79 out of 5 average rating, 136 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Apartment in Chicago
4.89 out of 5 average rating, 245 reviewsModern
Apartment in Irving Park
4.89 out of 5 average rating, 179 reviewsHistoric Chicago neighborhood flat
Apartment in Chicago
4.82 out of 5 average rating, 275 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Chicago
4.82 out of 5 average rating, 114 reviewsCozy Avondale apt right by Belmont blue line stop
Quick stats about apartment rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
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