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Search results; Over 1,000 homes in Chicago

Guest favorite
Loft in Chicago
Exposed brick loft near Wrigley Field
2 bedrooms, 2 beds, 2 private baths
Nov 1 – 6
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4.89 out of 5 average rating, 885 reviews
Guest favorite
Apartment in Chicago
Newly renovated near Millennium Park
4.9 out of 5 average rating, 128 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
Apartment in Oak Park
Renovated treetop retreat near Frank Lloyd Wright
4.98 out of 5 average rating, 94 reviews, 2 bedrooms, 4 beds, 1 bath
Nov 1 – 6
Top guest favorite
Apartment in Chicago
New-construction studio near Armitage shopping
5.0 out of 5 average rating, 318 reviews, 1 bedroom, 1 bed, 1 bath
Nov 30 – Dec 5
Guest favorite
Apartment in Chicago
Streeterville apartment near the lakefront
4.87 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Top guest favorite
Apartment in Forest Park
1908 home with 10-foot ceilings near Oak Park
4.98 out of 5 average rating, 417 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 23 – 28
Guest favorite
Apartment in Chicago
Speakeasy-chic brownstone near Lake Michigan
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 16 – 21
Top guest favorite
Condo in Chicago
11-foot ceilings and exposed brick walls
4.99 out of 5 average rating, 348 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 13 – 18
Top guest favorite
Rooms in Chicago
Historic 1896 home in North Park
4.97 out of 5 average rating, 119 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 20 – 25
Room in Chicago
Original woodwork and a back patio
New place to stay, 1 queen bed, 1 bath
Sep 6 – 11
Top guest favorite
Apartment in Chicago
Loft with a baby grand and game room
4.97 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Top guest favorite
Apartment in Chicago
Sun-drenched with garden views and fire pit
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 2 beds, 1.5 baths
Nov 1 – 6
Top guest favorite
Loft in Chicago
Vintage Chicago theme, walk to Wrigley
4.96 out of 5 average rating, 597 reviews, 1 bedroom, 2 beds, 1 bath
Nov 21 – 26
Guest favorite
Room in Alsip
Italy-inspired room with a back deck
4.91 out of 5 average rating, 276 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Guest favorite
Apartment in Chicago
Lofted art house near the beach
4.96 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bath
Sep 20 – 25
Top guest favorite
Apartment in Chicago
Soaring ceilings and skylights in Pilsen
4.98 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Top guest favorite
Condo in Chicago
Penthouse with private rooftop skyline views
4.93 out of 5 average rating, 222 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 7 – 12
Top guest favorite
Apartment in Chicago
Sun-drenched loft-like condo in Roscoe Village
4.95 out of 5 average rating, 269 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Top guest favorite
Room in Chicago
Walk to Wrigley from historic Lakeview
4.96 out of 5 average rating, 209 reviews, 2 single beds, 2.5 baths
Sep 6 – 11