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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Bright, Modern Apartment in a Vintage Greystone
1 bedroom, 2 beds, 1 private bathroom
28 Aug – 2 Sept
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4.92 out of 5 average rating, 435 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
23–28 Jul
4.97 out of 5 average rating, 95 reviews
Flat in Skokie
Skokie Serenity - 3 queen beds
3 bedrooms, 3 queen beds
26–31 Jul
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Place to stay in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 bedroom, 1 king bed
10–15 Aug
New place to stay
Top guest favourite
Flat in Forest Park
Walk to Dining & L Train • King Bed • Patio
2 bedrooms, 2 beds
16–21 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
22–27 Jul
4.96 out of 5 average rating, 161 reviews
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
1 bedroom, 1 king bed
17–22 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds
26–31 Jul
4.94 out of 5 average rating, 16 reviews
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
23–28 Aug
4.9 out of 5 average rating, 122 reviews
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 87 reviews
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed
24–29 Oct
4.9 out of 5 average rating, 49 reviews
Guest favourite
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
1 bedroom, 1 queen bed
21–26 Jul
5.0 out of 5 average rating, 11 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews