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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 158 reviews
Top guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
New place to stay
Flat in Chicago
3BR Vintage Apt • Patio • Walk to McKinley Park
3 bedrooms, 3 queen beds, 1 bathroom
21–26 Jun
New place to stay
Flat in Chicago
Bronzeville Oasis
1 bedroom, 3 beds, 1 bathroom
23–28 Jun
New place to stay
Top guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 423 reviews
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds, 1 bathroom
7–12 Aug
4.95 out of 5 average rating, 676 reviews
Superhost
Flat in Clarendon Hills
Clarendon Hills Apartment
2 bedrooms, 2 beds, 1.5 bathrooms
28 Jun – 3 Jul
New place to stay
Top guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Flat in Chicago
Well Located Studio on the Red Line
1 queen bed, 1 bathroom
5–10 Jul
New place to stay
Superhost
Flat in Chicago
Corporate Smart Home At River Walk
1 bedroom, 1 queen bed, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Jun – 3 Jul
4.99 out of 5 average rating, 299 reviews
Top guest favourite
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.96 out of 5 average rating, 580 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 61 reviews
Top guest favourite
Guest suite in Chicago
Chicago Neighborhood Private Guest Studio
2 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 496 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Room in Evanston
Welcoming Evanston Home
1 queen bed, 1 bathroom
9–14 Jul
4.94 out of 5 average rating, 239 reviews
Place to stay in Chicago
Private Room for 3 Guests By Grand Ave Blueline
1 bedroom, 2 beds, 2 bathrooms
4–9 Jul