filters

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
,
4.91 out of 5 average rating, 622 reviews
Top guest favourite
Home in South Side
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
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Flat in Little Italy
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
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 119 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds
29 Sept – 4 Oct
New place to stay
Top guest favourite
Bungalow in Beverly
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
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Ukrainian Village
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
Guest favourite
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
3–8 Aug
4.94 out of 5 average rating, 66 reviews
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Belmont Cragin
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Downtown 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
Guest favourite
Flat in South Side
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews