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Search results; Over 1,000 homes in Chicago

Guest favourite
Place to stay in South Side
Private Unit 001, McCormick, Chinatown, SOX, Grant Park
1 bedroom, 1 bed, 1 private bathroom
6–11 Aug
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4.94 out of 5 average rating, 224 reviews
Top guest favourite
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 12 reviews
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 West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 119 reviews
Apartment in Wicker Park
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds
17–22 Aug
New place to stay
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
13–18 Aug
5.0 out of 5 average rating, 7 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 West Side
Beautiful Chicago Greystone
4 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 142 reviews
Guest favourite
Flat in South Side
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
Guest favourite
Flat in Downtown 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
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
9–14 Aug
4.93 out of 5 average rating, 234 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, 27 reviews
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Logan Square
Spacious 3BR • Great for Groups • Fast WiFi • Pets
3 bedrooms, 3 queen beds
20–25 Oct
4.96 out of 5 average rating, 118 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
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 West Side
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds
21–26 Jul
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Albany Park
NorthSide Chicago duplex 5-BD,2King size-free park
5 bedrooms, 6 beds
29 Aug – 3 Sept
4.97 out of 5 average rating, 199 reviews
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
2 bedrooms, 2 beds
8–13 Sept
4.92 out of 5 average rating, 51 reviews