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
4.91 out of 5 average rating, 372 reviewsThe Grotto of Logan Square
Apartment in Chicago
4.89 out of 5 average rating, 370 reviewsGreat Location Studio in the Gold Coast!!
Apartment in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.98 out of 5 average rating, 130 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment in Chicago
4.95 out of 5 average rating, 108 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.96 out of 5 average rating, 256 reviewsLogan Square 2nd Floor Chicago Victorian
Apartment in Chicago
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Weekly apartment rentals
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Apartment in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Apartment in Chicago
4.92 out of 5 average rating, 491 reviews2BR Bursting w/ Character in Hip Logan Square!
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 234 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Apartment in Logan Square
4.87 out of 5 average rating, 486 reviewsLogan Square Studio
Apartment in Chicago
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Forest Park
4.93 out of 5 average rating, 585 reviewsPeaceful oasis in Forest Park
Private apartment rentals
Apartment in Chicago
4.87 out of 5 average rating, 272 reviewsHistoric Old Town Flat - Minutes from Downtown!
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 202 reviewsSpectacular Pilsen Studio for 2!
Apartment in Chicago
4.78 out of 5 average rating, 217 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Apartment in Park Ridge
4.79 out of 5 average rating, 322 reviewsModern Garden apartment (WHOLE UNIT)
Apartment in Logan Square
4.81 out of 5 average rating, 105 reviewsWelcome Chez Moi
Apartment in Chicago
4.98 out of 5 average rating, 250 reviewsAndersonville Cozy 1 bedroom basement suite
Apartment in Chicago
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment in Chicago
4.96 out of 5 average rating, 23 reviewsLincoln Square Oasis - Bright, clean 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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