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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Cozy 2 bdrm near McCormick Place & Wintrust Arena
2 bedrooms, 2 beds, 1 private bathroom
11–16 Nov
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4.94 out of 5 average rating, 183 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
19–24 Aug
New place to stay
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
7–12 Sept
New place to stay
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
22–27 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
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
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
22–27 Aug
4.93 out of 5 average rating, 243 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
2–7 Nov
4.96 out of 5 average rating, 310 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
23–28 Aug
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 121 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 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
Top guest favourite
Flat in Chicago
Skyline Views • Rooftop • Free EV Garage Parking
2 bedrooms, 8 beds
23–28 Aug
4.94 out of 5 average rating, 67 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, 919 reviews