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Search results; Over 1,000 homes in Chicago

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Flat in Chicago
Spectacular 2BR Penthouse in the Loop | Roof Deck
2 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
,
4.81 out of 5 average rating, 349 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
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 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
Guest favourite
Room in Chicago
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
1 queen bed, 1.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 52 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
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
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
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, 77 reviews
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 526 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
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 15 reviews
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 Oak Park
Open & Sunny Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 344 reviews