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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
1 bedroom, 2 beds, 1.5 private bathrooms
24–29 Oct
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4.98 out of 5 average rating, 269 reviews
Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Aug
New place to stay
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
7–12 Sept
New place to stay
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
22–27 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
20–25 Sept
New place to stay
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 243 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
28 Aug – 2 Sept
4.88 out of 5 average rating, 139 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds
18–23 Oct
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
1–6 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Flat in Chicago
Spacious 1BR | Washer/Dryer | Near Lincoln Square
1 bedroom, 1 bed
30 Aug – 4 Sept
4.89 out of 5 average rating, 9 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
Superhost
Flat in Chicago
2,109 Sq Ft Sky Suite | 62nd Fl | Lake Views
3 bedrooms, 4 beds
22–27 Aug
New place to stay
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed
8–13 Nov
4.97 out of 5 average rating, 919 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 63 reviews
Guest favourite
Apartment in Chicago
UChicago Condo | 2 Baths, Private Parking & Entry
1 bedroom, 1 queen bed
23–28 Aug
4.94 out of 5 average rating, 67 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
23–28 Aug
4.91 out of 5 average rating, 43 reviews
Guest favourite
Apartment in Chicago
12 Min Downtown, Free Parking, Rooftop, Sleeps 11
2 bedrooms, 8 beds
20–25 Aug
4.89 out of 5 average rating, 35 reviews