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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Lincoln Park
Private Lincoln Park Condo with 2 Parking Spots
4 bedrooms, 4 beds, 1 private bathroom
7–12 Sept
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4.97 out of 5 average rating, 139 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 81 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Flat in Rogers Park Township
2BR/1BA Apt w/ Modern Amenities Rogers Park
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
4.95 out of 5 average rating, 107 reviews, 3 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Luxe
Flat in Chicago Loop
Luxury Downtown 4BR | Exclusive Design PH
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
6–11 Jul
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Place to stay in Norwood Park
The Native Garden at the City's Edge
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Aug
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Superhost
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.89 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Updated Condo with Free Parking
5.0 out of 5 average rating, 101 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
4.98 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
21–26 Sept