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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Chicago
NEW luxury Old Town 1-Bedroom condo
1 bedroom, 1 bed, 1 shared bathroom
19–24 Sept
,
4.94 out of 5 average rating, 140 reviews
Top 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
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
Top guest favourite
Bungalow in Chicago
Game basement and fire pit in Beverly
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
Top guest favourite
Flat in Chicago
Minimal duplex with free private parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Flat in Chicago
Pilsen flat with a patio and fireplace
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Top guest favourite
Flat in Chicago
Roomy and Comfortable Apartment with everything UN
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Home in Chicago
Modern 3BR Near Obama Center, UChicago & McCormick
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Chicago
Designer loft with views in Gold Coast
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept
Top guest favourite
Flat in Chicago
Double-height windows in a Pilsen duplex
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Aug
Guest favourite
Flat in Berwyn
Remodeled with a backyard game room
4.91 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Chicago
Spacious garden apartment in Bronzeville
4.98 out of 5 average rating, 183 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Guest favourite
Home in Chicago
1890 greystone with a fire pit
4.94 out of 5 average rating, 142 reviews, 4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Guest favourite
Flat in Evanston
Renovated and soundproofed near Northwestern
4.92 out of 5 average rating, 191 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
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