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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Uptown
Cozy loft in Chicago's Uptown
1 bedroom, 2 beds, 1 private bathroom
26–31 Oct
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4.97 out of 5 average rating, 342 reviews
Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
20–25 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 Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
7–12 Sept
New place to stay
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
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.92 out of 5 average rating, 71 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
24–29 Nov
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 137 reviews
Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 1 bed, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
4.96 out of 5 average rating, 597 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Top guest favourite
Flat in Lake View
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 269 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 37 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 North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Bridgeport
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
Guest favourite
Flat in Downtown Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 123 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