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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Gorgeous Penthouse with Stunning Views from Private Rooftop
2 bedrooms, 2 beds, 2 private bathrooms
18–23 Jul
,
4.9 out of 5 average rating, 312 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
Flat in Chicago
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
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, 12 reviews
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 142 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
3–8 Aug
4.94 out of 5 average rating, 66 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
13–18 Aug
5.0 out of 5 average rating, 7 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 Chicago
Modern 3BR Apartment Near North Ave Shops
3 bedrooms, 3 double beds
20–25 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
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
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
Flat in Chicago
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
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 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
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
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
29 Sept – 4 Oct
New place to stay
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