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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in West Town
The Woodsman's Gallery at OHC
3 bedrooms, 4 beds, 2 private bathrooms
26–31 Jul
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4.9 out of 5 average rating, 621 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 12 beds, 3.5 bathrooms
2–7 Jul
4.95 out of 5 average rating, 40 reviews
Townhouse in West Side
Walk to United Center 9 mins-Downtown FreeParking
3 bedrooms, 3 beds, 3 bathrooms
5–10 Jul
4.75 out of 5 average rating, 8 reviews
Home in West Side
Big Group Stay-Private Yard/Parking/MillenniumPark
5 bedrooms, 8 beds, 3.5 bathrooms
9–14 Sept
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
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
2–7 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in South Side
The Langley Luxe modern style unit
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Bridgeport
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
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, 7 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 5 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
Flat in Downtown Chicago
Gold Coast Gem
2 bedrooms, 3 queen beds, 2 bathrooms
2–7 Jul
New place to stay
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
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.94 out of 5 average rating, 66 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