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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in West Town
Modern/Spacious 2BR/2BA West Town
2 bedrooms, 2 beds, 2 private bathrooms
4–9 Oct
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4.93 out of 5 average rating, 293 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, 130 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 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 Chicago Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
19–24 Aug
New place to stay
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 166 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
Room in Bridgeport
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
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
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
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 22 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
Superhost
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Superhost
Flat in Chicago Loop
The Horizon | 3BR PH, 63rd Fl, Top Sky Deck
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
New place to stay
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 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, 12 reviews
Top guest favourite
Apartment in Uptown
Near Lake Michigan & Wrigley Field
2 bedrooms, 2 king beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 359 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, 310 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 918 reviews