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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Clean & Bright Chicago Condo - FREE Parking Spot
2 bedrooms, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.77 out of 5 average rating, 601 reviews
Superhost
Home in Schaumburg
Chicagoland-Schaumburg/ORD 3BR Ranch Home, sleeps7
3 bedrooms, 4 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.94 out of 5 average rating, 464 reviews
Top guest favourite
Flat in Chicago
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 124 reviews
Flat in Chicago
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 Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 54 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
New place to stay
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
11–16 Jul
4.93 out of 5 average rating, 231 reviews
Top guest favourite
Flat in Chicago
Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
4.93 out of 5 average rating, 335 reviews
Guest favourite
Flat in Chicago
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, 6 reviews
Top guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 36 reviews
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
6–12 Jul
New place to stay