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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Chicago
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
2 bedrooms, 2 beds, 2 private bathrooms
27 Sept – 2 Oct
,
4.92 out of 5 average rating, 124 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 168 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed, Parking, Deck, Yard
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 99 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
7–12 Sept
4.91 out of 5 average rating, 81 reviews
Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds
7–12 Dec
4.94 out of 5 average rating, 582 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
14–19 Oct
4.88 out of 5 average rating, 445 reviews
Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 207 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews