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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bedroom, 1 bed, 1 shared bathroom
16–21 Aug
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4.9 out of 5 average rating, 597 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
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, 1 bathroom
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.95 out of 5 average rating, 164 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 412 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed, 1 bathroom
24–29 Oct
4.9 out of 5 average rating, 50 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 118 reviews
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 101 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 bathroom
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, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Guest favourite
Room in Evanston
Welcoming Evanston Home
1 queen bed, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 248 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH1 - Fulton Market
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
New place to stay
Top guest favourite
Room in Chicago
The Native Garden at the City's Edge
1 queen bed, 1 bathroom
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 bathroom
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, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews