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Search results; Over 1,000 homes in Chicago

Superhost
Apartment in West Side
The Upscale Getaway Near Downtown
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Oct
,
4.93 out of 5 average rating, 296 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 130 reviews
Room in Downtown Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.75 out of 5 average rating, 16 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, 127 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 70 reviews
Superhost
Flat in West Town
Luxury Penthouse Collection PH2 - Fulton Market
1 bedroom, 2 beds, 1 bathroom
7–13 Sept
New place to stay
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 35 reviews
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Room in Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 25 reviews
Room in Bridgeport
Bridgeport Chicago near everything affordable.-5
1 double bed, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Downtown Chicago
Chic 2BR Gem with Fireplace
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 160 reviews
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 87 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
4.95 out of 5 average rating, 109 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Bridgeport
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in West Loop
West Loop 2BR : Skyline Views + Prime Location
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 69 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 309 reviews