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Search results; Over 1,000 homes in Chicago

Top guest favorite
This Uptown loft in a vintage Queen Anne puts you near the Green Mill
1 bedroom, 2 beds, 1 private bath
Nov 9 – 14
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4.97 out of 5 average rating, 341 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
Top guest favorite
This Wicker Park condo gives you free parking, a fireplace, and a private entrance
4.97 out of 5 average rating, 917 reviews, 1 bedroom, 1 bed, 1 bath
Nov 4 – 9
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
This Cicero apartment puts you minutes from downtown Chicago
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bath
Oct 25 – 30
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
Private room
A peaceful, centrally located private room in Bridgeport awaits you
New place to stay, 1 double bed, 1 bath
Aug 22 – 27
Top guest favorite
This freshly remodeled Lakeview loft gives you a private patio and vintage Chicago charm
4.96 out of 5 average rating, 597 reviews, 1 bedroom, 2 beds, 1 bath
Nov 21 – 26
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
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
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
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 minimal Bridgeport duplex gives you two floors and free private parking
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
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, 691 reviews, 3 beds, 1 bath
Nov 17 – 22
Top guest favorite
This 1908 coach house gives you skyline views from a rooftop deck in Humboldt Park
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 baths
Nov 15 – 20
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