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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Grace House | Cozy, contemporary + convenient 2-BR
2 bedrooms, 2 beds, 1 private bathroom
17–22 Aug
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4.98 out of 5 average rating, 125 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 118 reviews
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
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
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
23–28 Oct
4.98 out of 5 average rating, 412 reviews
Top guest favourite
Room in Chicago
Rogers Park Penthouse
1 bed, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 107 reviews
Place to stay in Chicago
Charming Room in Historic Ukrainian Village!
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
New place to stay
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
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Flat in Chicago
Andersonville Garden Living
1 bedroom, 3 double beds, 1 bathroom
20–25 Sept
4.83 out of 5 average rating, 150 reviews
Superhost
Guest house in Chicago
Horner Park Coach House
1 bedroom, 1 bed, 1 bathroom
19–24 Oct
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 93 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed, 1 bathroom
25–30 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, 102 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, 52 reviews
Top guest favourite
Room in Chicago
West Beverly’s Gem-Private bedroom #1
1 queen bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 98 reviews
Top 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
Top guest favourite
Apartment in Chicago
Susie's Space. 2BR easy parking & pet friendly
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 391 reviews