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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Close to coffee, commuting, restaurants & bars
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 284 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
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
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Flat in Chicago
Spacious, Charming, Top Floor, Steps to Wrigley
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Superhost
Flat in Chicago
3 bed Bucktown Duplex, next to the 606 bike trail
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 4 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, 117 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from a Cozy, Sun-soaked Hideaway
2 bedrooms, 3 beds, 1 bathroom
7–12 Dec
4.96 out of 5 average rating, 242 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
New place to stay
Flat in Chicago
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Sept
New place to stay
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
Superhost
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in Chicago
Best City Views • Rooftop Nights • EV Garage Free
2 bedrooms, 6 beds, 2 bathrooms
7–12 Aug
4.98 out of 5 average rating, 90 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
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 30 reviews
Superhost
Flat in Chicago
Brown Line Lounge | Curated Moody
3 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Chicago
Private Bedroom By O’hare (Norwood Park)
1 bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 9 reviews