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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
1,800ft² Parking Workspace W/D Full Kitch
2 bedrooms, 4 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.99 out of 5 average rating, 215 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds
17–22 Aug
New place to stay
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 118 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 5 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
Flat in Chicago
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds
10–15 Sept
New place to stay
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
6–11 Aug
4.91 out of 5 average rating, 117 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
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
26–31 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Oak Park
Stylish & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
26–31 Oct
5.0 out of 5 average rating, 91 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, 165 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
8–13 Aug
4.91 out of 5 average rating, 43 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
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 26 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews