filters

Search results; Over 1,000 homes in Chicago

Guest favourite
Place to stay in Chicago
Private penthouse suite with skyline view
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
,
4.84 out of 5 average rating, 449 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 22 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
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 141 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
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds
6–11 Aug
New place to stay
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
18–23 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
2–7 Aug
4.91 out of 5 average rating, 74 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms
16–21 Aug
4.95 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews