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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 beds, 1 private bathroom
23–28 Nov
,
4.99 out of 5 average rating, 953 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
7–12 Aug
New place to stay
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds
17–22 Oct
4.98 out of 5 average rating, 412 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.95 out of 5 average rating, 164 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 50 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed
4–9 Oct
4.95 out of 5 average rating, 118 reviews
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds
21–26 Oct
4.94 out of 5 average rating, 472 reviews
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Room in Chicago
The Native Garden at the City's Edge
1 queen bed
1–6 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Forest Park
Cheerful Remodel Prime Location
1 bedroom, 1 queen bed
1–6 Nov
4.92 out of 5 average rating, 148 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
9–14 Aug
4.91 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds
16–21 Aug
4.93 out of 5 average rating, 344 reviews
Top guest favourite
Flat in Oak Park
Open & Sunny Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
19–24 Sept
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed
12–17 Oct
4.94 out of 5 average rating, 448 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 47 reviews