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Search results; Over 1,000 homes in Chicago

Top guest favorite
Apartment in Chicago
Private deck with a grill near Wrigley
2 bedrooms, 2 beds, 1 bath
Aug 17 – 22
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4.99 out of 5 average rating, 162 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
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
Top guest favorite
Apartment in Forest Park
1908 home with 10-foot ceilings near Oak Park
4.98 out of 5 average rating, 415 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 23 – 28
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, 34 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
Guest favorite
Apartment in Chicago
Speakeasy-chic brownstone near Lake Michigan
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 1.5 baths
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
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
Loft in Chicago
Vintage Chicago theme, walk to Wrigley
4.96 out of 5 average rating, 595 reviews, 1 bedroom, 2 beds, 1 bath
Dec 13 – 18
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
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
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
Apartment in Chicago
Hardwood floors and a spa-style bathroom
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 20 – 25
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 flat above a neighborhood tavern
4.99 out of 5 average rating, 359 reviews, 3 bedrooms, 4 beds, 1 bath
Sep 27 – Oct 2