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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
2-Story Penthouse Views, Fireplace, Pool, Gym
2 bedrooms, 4 beds, 3 private bathrooms
26 Sept – 1 Oct
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4.91 out of 5 average rating, 44 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
1–6 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
20–25 Aug
4.89 out of 5 average rating, 134 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
23–28 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
19–24 Aug
New place to stay
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Oct – 1 Nov
4.95 out of 5 average rating, 166 reviews
Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed
19–24 Oct
5.0 out of 5 average rating, 5 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 30 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 60 reviews
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
18–23 Aug
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed
8–13 Nov
4.97 out of 5 average rating, 918 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews