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Search results; Over 1,000 homes in Chicago

Top guest favorite
This contemporary West Loop apartment gives you 10ft ceilings and a private balcony
2 bedrooms, 3 beds, 2 private baths
Sep 28 – Oct 4
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4.94 out of 5 average rating, 146 reviews
Guest favorite
This newly renovated downtown Chicago apartment puts you near Millennium Park
4.9 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Guest favorite
Eclectic decor and open-concept living greet you at this modern Pilsen apartment
4.95 out of 5 average rating, 127 reviews, 2 bedrooms, 3 beds, 1.5 baths
Dec 27 – Jan 1
Superhost
Vintage meets modern at this chic Logan Square condo — you’ll love the vibe
2 bedrooms, 2 beds, 1 bath
Oct 18 – 23
Top guest favorite
This two-level Pilsen coach house gives you a private entrance and vibrant murals nearby
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bath
Sep 27 – Oct 2
Top guest favorite
Double-height ceilings and floor-to-ceiling windows greet you at this Pilsen duplex
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 17 – 22
Private room
A peaceful, centrally located private room in Bridgeport awaits you
New place to stay, 1 double bed, 1 bath
Aug 22 – 27
Guest favorite
This historic Chicago bungalow gives you a backyard, workspace, and multiple sitting areas
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 28 – Oct 3
Guest favorite
This Norwood Park apartment gives you a private entrance and open-concept layout
4.88 out of 5 average rating, 441 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Sun-filled windows and a record player greet you at this Wrigley condo
4.99 out of 5 average rating, 169 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 29 – Dec 4
Top guest favorite
Sun-drenched and loft-like, this Roscoe Village condo gives you a private entrance
4.95 out of 5 average rating, 269 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
A baby grand piano and arcade game room await you at this Avondale loft
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Guest favorite
This Bucktown duplex gives you a 700-sq-ft roof deck and the 606 trail steps away
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1 bath
Aug 28 – Sep 2
Top guest favorite
This West Loop penthouse gives you skyline views from a private rooftop deck
5.0 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 20 – 25
Superhost
This Fulton Market penthouse gives you city views from a shared rooftop with fire pits
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 7 beds, 2 baths
Sep 23 – 28
Superhost
Floor-to-ceiling windows and a private terrace give you cityscape views at this River North loft
4.9 out of 5 average rating, 122 reviews, 3 bedrooms, 8 beds, 3 baths
Nov 1 – 6
Guest favorite
This spacious Streeterville apartment puts you near Lake Michigan with an outdoor terrace
4.87 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Guest favorite
Skylights and soaring ceilings greet you at this Bronzeville penthouse with a jacuzzi
4.96 out of 5 average rating, 70 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 27 – Oct 2
Top guest favorite
A newly built Lincoln Park studio where you’ll enjoy all-new furnishings
5.0 out of 5 average rating, 318 reviews, 1 bedroom, 1 bed, 1 bath
Nov 30 – Dec 5