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Search results; Over 1,000 homes in Chicago

Top guest favorite
Apartment in Chicago
Classic 2-flat steps from Clark Street
3 bedrooms, 4 beds, 1 private bath
Sep 13 – 18
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4.99 out of 5 average rating, 130 reviews
Guest favorite
Apartment in Chicago
Newly renovated near Millennium Park
4.9 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
Condo in Chicago
Wicker Park with free parking
4.97 out of 5 average rating, 917 reviews, 1 bedroom, 1 bed, 1 bath
Nov 4 – 9
Guest favorite
Guest suite in Chicago
Open-concept layout near O’Hare airport
4.88 out of 5 average rating, 441 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
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, 416 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 23 – 28
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
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
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
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
Guest favorite
Apartment in Chicago
Original woodwork in walkable Lincoln Square
4.92 out of 5 average rating, 171 reviews, 3 bedrooms, 4 beds, 1 bath
Oct 24 – 29
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
Apartment in Oak Park
In the Frank Lloyd Wright District
4.95 out of 5 average rating, 205 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Top guest favorite
Home in Chicago
Sun-filled modern home in Bridgeport
4.96 out of 5 average rating, 309 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 11 – 16
Room in Chicago
Original woodwork and a back patio
New place to stay, 1 queen bed, 1 bath
Sep 6 – 11
Top guest favorite
Room in Chicago
Historic 1893 home near Wrigley Field
4.87 out of 5 average rating, 271 reviews, 1 queen bed, 1 bath
Aug 16 – 21
Top guest favorite
Apartment in Chicago
Renovated flat with free on-site parking
4.92 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 27 – Oct 2
Superhost
Apartment in Oak Park
New build near the Blue Line
4.83 out of 5 average rating, 115 reviews, 1 bedroom, 1 bed, 1 bath
Aug 30 – Sep 4