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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Great location, private entry and patio!
1 bedroom, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 347 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.97 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 54 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Superhost
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
4.9 out of 5 average rating, 122 reviews, 3 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
5.0 out of 5 average rating, 87 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Flat in Forest Park
Walk to Dining & L Train • King Bed • Patio
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Place to stay in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
New place to stay, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
4.93 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct