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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 159 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
12–17 Jul
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 118 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed
19–24 Sept
4.94 out of 5 average rating, 139 reviews
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds
22–27 Aug
New place to stay
Top guest favourite
Room in Chicago
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
3 beds
25–30 Oct
4.95 out of 5 average rating, 678 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
New place to stay
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
4–9 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Room in Chicago
Comfortable bed with Smart stand
1 queen bed
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 80 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed
24–29 Oct
4.89 out of 5 average rating, 45 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
1–6 Jul
4.97 out of 5 average rating, 73 reviews
Guest favourite
Flat in Chicago
West Loop 2BR : Skyline Views + Prime Location
2 bedrooms, 3 beds
2–7 Jul
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
16–21 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom, 1 king bed
25–30 Oct
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Oak Park
Top Floor Roomy Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
17–22 Aug
4.98 out of 5 average rating, 82 reviews