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
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Apartment in Oak Park
4.89 out of 5 average rating, 334 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Apartment in Forest Park
5.0 out of 5 average rating, 221 reviewsLike a Treehouse!
Apartment in Near North Side
4.9 out of 5 average rating, 372 reviewsGreat Location Studio in the Gold Coast!!
Apartment in Chicago
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Apartment in Chicago
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Apartment in Logan Square
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Apartment in Chicago
4.96 out of 5 average rating, 257 reviewsLogan Square 2nd Floor Chicago Victorian
Weekly apartment rentals
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
Apartment in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
Apartment in Andersonville
4.98 out of 5 average rating, 250 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Forest Park
4.93 out of 5 average rating, 585 reviewsPeaceful oasis in Forest Park
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in Chicago
4.98 out of 5 average rating, 130 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Chicago
4.85 out of 5 average rating, 184 reviewsBucktown Retreat - Why The Buck Not? Sleeps 1-6
Private apartment rentals
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Apartment in Chicago
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Apartment in Chicago
4.82 out of 5 average rating, 436 reviewsLovely Andersonville Apt with Ideal Location
Apartment in Chicago
4.81 out of 5 average rating, 105 reviewsWelcome Chez Moi
Apartment in Chicago
4.99 out of 5 average rating, 181 reviewsNW Chicago Apartment in Safe Neighborhood
Apartment in Chicago
4.95 out of 5 average rating, 172 reviewsWicker Park/Bucktown Location
Apartment in Oak Park
4.97 out of 5 average rating, 163 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Chicago
4.87 out of 5 average rating, 486 reviewsLogan Square Studio
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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