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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in West Loop
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Aug
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4.97 out of 5 average rating, 38 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Superhost
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Top guest favourite
Flat in Lake View
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 268 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 915 reviews
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 356 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
4.96 out of 5 average rating, 595 reviews
Guest favourite
Flat in Chicago Loop
Downtown Penthouse Huge Patio with Great View
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 79 reviews
Superhost
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
23–28 Aug
New place to stay
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Inn. Historic Greystone. Parking pass
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 174 reviews
Flat in South Side
Stylish Flat near Downtown,Obama Library, UChicago
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Sept
New place to stay
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 34 reviews
Flat in Logan Square
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in Ravenswood
Beautiful, sunny 2nd floor 3BR/1BA w free parking
3 bedrooms, 4 beds, 1 bathroom
24–29 Oct
4.93 out of 5 average rating, 170 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 305 reviews