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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 beds, 1 private bathroom
23–28 Nov
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4.99 out of 5 average rating, 956 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
18–23 Aug
4.9 out of 5 average rating, 130 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
16–21 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.-5
1 double bed
6–11 Sept
New place to stay
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 441 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Room in Chicago
Private Queen Bedroom with Private Bathroom
1 queen bed
17–22 Aug
4.95 out of 5 average rating, 205 reviews
Flat in Chicago
Bright & Cozy 1 Bdrm • Free Parking
1 bedroom, 2 beds
28 Sept – 3 Oct
4.57 out of 5 average rating, 58 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 26 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
17–22 Aug
4.71 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed
1–6 Oct
4.96 out of 5 average rating, 94 reviews
Guest favourite
Flat in Chicago
Skyline Views • Rooftop • Free EV Garage Parking
2 bedrooms, 8 beds
16–21 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Room in Chicago
The Champlain Suite
1 bed
16–21 Aug
4.95 out of 5 average rating, 41 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed
31 Oct – 5 Nov
4.95 out of 5 average rating, 120 reviews
Guest favourite
Flat in Chicago
West Loop 2BR : Skyline Views + Prime Location
2 bedrooms, 3 beds
16–21 Aug
4.97 out of 5 average rating, 69 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
16–21 Aug
New place to stay
Top guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 13 reviews