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Search results; Over 1,000 homes in Chicago

Superhost
Apartment in Chicago
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
3 bedrooms, 3 beds, 2 private bathrooms
20–25 Aug
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4.9 out of 5 average rating, 115 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
19–24 Aug
New place to stay
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
7–12 Sept
New place to stay
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
4.95 out of 5 average rating, 130 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
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, 2 bathrooms
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, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Chicago
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
Guest favourite
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 310 reviews
Superhost
Flat in Chicago
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
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 Chicago
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 Chicago
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
Top guest favourite
Flat in Chicago
Skyline Views • Rooftop • Free EV Garage Parking
2 bedrooms, 8 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 67 reviews