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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Town
Sun-Soaked West Loop Penthouse/Private Rooftop/3BA
2 bedrooms, 4 beds, 3 private bathrooms
17–22 Aug
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5.0 out of 5 average rating, 75 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.89 out of 5 average rating, 133 reviews
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
23–28 Aug
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 Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
19–24 Aug
New place to stay
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, 17 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 28 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
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
6–11 Sept
New place to stay
Flat in Wrigleyville
2,400 SF 4BR + 2 Parking | Steps to Wrigley
4 bedrooms, 6 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 1 bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 60 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Superhost
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Room in South Side
Room w/ Private Bath | Chicago IL
1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 119 reviews