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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
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4.99 out of 5 average rating, 957 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
20–25 Aug
New place to stay
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
7–12 Sept
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
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
29 Aug – 3 Sept
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
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
Apartment in Chicago
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 Chicago
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
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
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
Top guest favourite
Flat in Chicago
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
Room in Chicago
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
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, 19 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
21–26 Aug
New place to stay
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
Apartment in Chicago
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 Chicago
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