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Search results; Over 1,000 homes in Chicago

Guest favourite
Holiday home in South Side
UChicago Luxurious King Suite Lakefront
1 bedroom, 2 beds, 1 private bathroom
30 Sept – 5 Oct
,
4.95 out of 5 average rating, 98 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Room in The Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
6–11 Sept
New place to stay
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds
6–11 Sept
New place to stay
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
14–19 Oct
4.88 out of 5 average rating, 445 reviews
Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 58 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
6–11 Sept
New place to stay
Room in Downtown Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds
6–11 Sept
New place to stay
Top guest favourite
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
6–11 Sept
4.96 out of 5 average rating, 89 reviews
Superhost
Flat in Little Italy
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Nov – 2 Dec
4.95 out of 5 average rating, 171 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
25–30 Oct
4.97 out of 5 average rating, 32 reviews