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Search results; Over 1,000 homes in Chicago

This Bucktown apartment in a restored cottage puts you on a quiet tree-lined street
1 bedroom, 1 bed, 1 private bath
Nov 2 – 7
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4.82 out of 5 average rating, 594 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
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
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 1908 Forest Park apartment greets you with 10-foot ceilings and local art
4.98 out of 5 average rating, 416 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 23 – 28
Top guest favorite
This bright top-floor Oak Park apartment puts you among the treetops with a private deck
4.98 out of 5 average rating, 94 reviews, 2 bedrooms, 4 beds, 1 bath
Nov 1 – 6
Guest favorite
Speakeasy chic greets you at this Hyde Park brownstone garden apartment
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 16 – 21
Top guest favorite
This Lincoln Park condo gives you 11-foot ceilings, exposed brick, and hardwood floors
4.99 out of 5 average rating, 348 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 13 – 18
Guest favorite
Private room
This Alsip home’s Italy-inspired private room gives you a deck and office space
4.91 out of 5 average rating, 276 reviews, 1 queen bed, 1 bath
Aug 16 – 21
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
Top guest favorite
Original artwork fills this Wicker Park apartment -- and you get free parking
4.98 out of 5 average rating, 627 reviews, 1 bedroom, 1 bed, 1 bath
Oct 26 – 31
Guest favorite
A lofted Lincoln Park apartment in a historic building with art house decor
4.96 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bath
Sep 20 – 25
Top guest favorite
Sun-drenched Logan Square apartment where you’ll look out over a lush garden
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 2 beds, 1.5 baths
Nov 1 – 6
Top guest favorite
Skylights and soaring ceilings greet you at this art-filled Pilsen apartment
4.98 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Top guest favorite
Private room
This historic Lakeview home gives you a patio, pergola, and pool table
4.87 out of 5 average rating, 271 reviews, 1 queen bed, 1 bath
Aug 16 – 21
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
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
Granite countertops and a fireplace greet you at this Gold Coast apartment
4.98 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 2 baths
Sep 27 – Oct 2
Guest favorite
This Old Town Triangle house puts you in a historic building with a private entrance
4.95 out of 5 average rating, 189 reviews, 3 bedrooms, 3 beds, 1 bath
Oct 4 – 9