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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Urban Chic Apartment by the Magnificent Mile
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
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4.95 out of 5 average rating, 291 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
29 Aug – 3 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 140 reviews
Top guest favourite
Flat in Chicago
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
2–7 Aug
4.95 out of 5 average rating, 41 reviews
Guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
13–18 Aug
4.92 out of 5 average rating, 189 reviews
Guest favourite
Flat in Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds
21–26 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds
8–13 Nov
4.97 out of 5 average rating, 198 reviews
Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
4 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 18 reviews