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Search results; Over 1,000 homes in Chicago

Guest favorite
Room in Chicago
1903 Victorian half a block from beach
1 bedroom, 1 bed, 1 private bath
Sep 8 – 13
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4.94 out of 5 average rating, 51 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 12 – 17
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
Guesthouse in Chicago
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
Apartment in Cicero
Minutes from downtown Chicago with a washer
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bath
Aug 16 – 21
Guest favorite
Apartment in Chicago
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 Chicago
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
Room in Chicago
Brownstone suite with free bikes nearby Wrigley
4.95 out of 5 average rating, 690 reviews, 3 beds, 1 bath
Nov 17 – 22
Top guest favorite
Apartment in Chicago
Loft with a baby grand and game room
4.97 out of 5 average rating, 34 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 1 – 6
Top guest favorite
Condo in Chicago
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
Top guest favorite
Apartment in Chicago
Sun-drenched flat above a neighborhood tavern
4.99 out of 5 average rating, 359 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 27 – Oct 2
Top guest favorite
Condo in Chicago
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
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
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
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
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
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
Guest favorite
Apartment in Chicago
Designer loft 2 blocks from Michigan Ave
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
Apartment in Chicago
Minimal duplex with free private parking
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 23 – 28