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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Little Italy
Modern+Spacious Inn Little Italy Near W Loop W/PKG
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.99 out of 5 average rating, 328 reviews
Top guest favourite
Flat in North Side
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 336 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 9 reviews
Flat in Rogers Park Township
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.97 out of 5 average rating, 74 reviews
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.95 out of 5 average rating, 20 reviews
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
4–9 Sept
New place to stay
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 124 reviews
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 110 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Guest favourite
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Place to stay in Norwood Park
The Native Garden at the City's Edge
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Wicker Park
Division St Designer Home In Heart of Wicker Park
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.96 out of 5 average rating, 289 reviews
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 51 reviews