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Search results; Over 1,000 homes in Chicago

Top guest favorite
Bungalow in Lake View
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private baths
Aug 30 – Sep 4
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4.96 out of 5 average rating, 164 reviews
Guest favorite
Apartment in Chicago Loop
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 West Town
Wicker Park with free parking
4.97 out of 5 average rating, 917 reviews, 1 bedroom, 1 bed, 1 bath
Nov 1 – 6
Superhost
Condo in Logan Square
Vintage meets modern in Logan Square
2 bedrooms, 2 beds, 1 bath
Oct 18 – 23
Guest favorite
Apartment in West Side
Eclectic decor in Pilsen’s art district
4.95 out of 5 average rating, 127 reviews, 2 bedrooms, 3 beds, 1.5 baths
Dec 27 – Jan 1
Top guest favorite
Apartment in West Side
Double-height windows in a Pilsen duplex
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 17 – 22
Top guest favorite
Guesthouse in West Side
Private coach house in vibrant Pilsen
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bath
Sep 27 – Oct 2
Room in Bridgeport
Peaceful room in central Bridgeport
New place to stay, 1 double bed, 1 bath
Aug 22 – 27
Guest favorite
Home in Chicago
Historic bungalow with free parking near Hyde Park
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 28 – Oct 3
Top guest favorite
Condo in Lincoln Park
Walk to Wrigley with abundant light
4.99 out of 5 average rating, 169 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 29 – Dec 4
Top guest favorite
Apartment in Lake View
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
Guest favorite
Apartment in Wicker Park
Bucktown duplex with a 700-sq-ft roof deck
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1 bath
Aug 28 – Sep 2
Guest favorite
Guest suite in Norwood Park
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
Top guest favorite
Apartment in North Side
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
Condo in West Town
Penthouse with a private rooftop and grill
5.0 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 20 – 25
Superhost
Apartment in West Town
Penthouse with rooftop city views
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 7 beds, 2 baths
Sep 23 – 28
Superhost
Apartment in Downtown Chicago
Loft with a terrace and city views
4.9 out of 5 average rating, 122 reviews, 3 bedrooms, 8 beds, 3 baths
Nov 1 – 6
Guest favorite
Apartment in Downtown Chicago
Streeterville apartment near the lakefront
4.87 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Guest favorite
Apartment in South Side
Penthouse with skylights and a jacuzzi tub
4.96 out of 5 average rating, 70 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 27 – Oct 2