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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Modern+Spacious Inn Little Italy Near W Loop W/PKG
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.99 out of 5 average rating, 331 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
4.94 out of 5 average rating, 141 reviews, 1 single bed, 1 bathroom
19–24 Sept
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Flat in Chicago
2BR/1BA Apt w/ Modern Amenities Rogers Park
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Superhost
Place to stay in Chicago
Woodlawn Beauty: Room 2
4.4 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 1 bathroom
3–8 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
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 234 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Room in Chicago
Comfortable bed with Smart stand
5.0 out of 5 average rating, 5 reviews, 1 queen bed, 1 bathroom
18–23 Jul
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Guest favourite
Place to stay in Bridgeview
Comfortable Private Room with Easy Chicago Access
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 312 reviews, 1 queen bed, 1 bathroom
5–10 Nov
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
4.99 out of 5 average rating, 94 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Chicago
Modern 3BR Apartment Near North Ave Shops
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul