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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Bridgeport
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
2 bedrooms, 3 beds, 2.5 private bathrooms
12–17 Oct
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4.96 out of 5 average rating, 182 reviews
Guest favourite
Flat in South Side
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 167 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Room in The Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
14–19 Oct
4.88 out of 5 average rating, 445 reviews
Top guest favourite
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Bridgeport
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Irving Park
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds, 2.5 bathrooms
8–13 Nov
4.98 out of 5 average rating, 61 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Irving Park
Sports Fans Welcome and Family Friendly
3 bedrooms, 8 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 25 reviews
Superhost
Flat in Little Italy
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Ravenswood
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 258 reviews
Guest favourite
Home in Lincoln Park
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.95 out of 5 average rating, 195 reviews