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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
,
4.99 out of 5 average rating, 957 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
7–12 Sept
New place to stay
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
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
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
22–27 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
23–28 Aug
4.89 out of 5 average rating, 137 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
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
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 166 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
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
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 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, 120 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
Guest favourite
Room in Chicago
Private Bedroom By O’hare (Norwood Park)
1 bed
5–10 Sept
5.0 out of 5 average rating, 12 reviews