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Search results; Over 1,000 homes in Chicago

Top guest favorite
Vaulted ceilings and skylights fill this Lincoln Park cottage with light
1 bedroom, 2 beds, 1 private bath
Sep 13 – 18
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4.94 out of 5 average rating, 36 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 12 – 17
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
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
This Cicero apartment puts you minutes from downtown Chicago
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 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
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
Top guest favorite
Private room
This Roscoe Village brownstone gives you a private entrance, bath, and free bikes
4.95 out of 5 average rating, 690 reviews, 3 beds, 1 bath
Nov 17 – 22
Top guest favorite
A baby grand piano and arcade game room await you at this Avondale loft
4.97 out of 5 average rating, 34 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
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
Top guest favorite
This sundrenched Ravenswood flat puts you above a beloved neighborhood tavern
4.99 out of 5 average rating, 359 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 27 – Oct 2
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
Private room
Original woodwork and a spacious patio greet you at this Ukrainian Village room
New place to stay, 1 queen bed, 1 bath
Sep 6 – 11
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
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
Natural light and local artwork fill this modern Bridgeport house you’ll love coming home to
4.96 out of 5 average rating, 309 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 11 – 16
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
Guest favorite
Full floor windows and a chef’s kitchen greet you at this River North loft
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
This minimal Bridgeport duplex gives you two floors and free private parking
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28