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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Ukrainian Village
Charming private coach house
1 bedroom, 2 beds, 1 private bathroom
8–13 Jul
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4.97 out of 5 average rating, 59 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 233 reviews
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
2 bedrooms, 3 queen beds, 2 bathrooms
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, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in West Side
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews
Guest favourite
Flat in South Side
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Humboldt Park
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds, 6 bathrooms
29 Aug – 3 Sept
4.8 out of 5 average rating, 10 reviews
Flat in West Rogers Park
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Flat in Downtown Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 9 reviews