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Search results; Over 1,000 homes in Chicago

Superhost
Hotel room in Wicker Park
Romantic Queen Room in Boutique Wicker Park B&B
1 bedroom, 1 bed, 2 private bathrooms
11–16 Dec
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5.0 out of 5 average rating, 6 reviews
Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
20–25 Aug
New place to stay
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
7–12 Sept
New place to stay
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
29 Aug – 3 Sept
New place to stay
Room in Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 919 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Flat in Wicker Park
Stylish 2BR stunner w/ unbeatable location
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 202 reviews
Guest favourite
Flat in Albany Park
Spacious 1BR | Washer/Dryer | Near Lincoln Square
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.89 out of 5 average rating, 9 reviews
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 63 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Room in Norwood Park
Private Bedroom By O’hare (Norwood Park)
1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Bridgeport
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Apartment in South Side
UChicago Condo | 2 Baths, Private Parking & Entry
1 bedroom, 1 queen bed, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 67 reviews
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in West Side
Millennium Park 10 Min, Parking, Balcony, Sleeps 8
2 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
4.96 out of 5 average rating, 169 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 57 reviews