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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
iKlektik House Chicago/BlueJay
1 bedroom, 1 bed, 1 private bathroom
23–28 Aug
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4.92 out of 5 average rating, 258 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 Sept
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4.94 out of 5 average rating, 141 reviews, 4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4.98 out of 5 average rating, 183 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
4.91 out of 5 average rating, 74 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 5 beds, 3.5 bathrooms
21–26 Sept
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct