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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
Penthouse Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.79 out of 5 average rating, 229 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
6–11 Jul
4.94 out of 5 average rating, 66 reviews
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
6–11 Jul
4.95 out of 5 average rating, 41 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
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
16–21 Aug
4.88 out of 5 average rating, 433 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 16 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
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, 26 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, 3 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
6–11 Aug
4.97 out of 5 average rating, 156 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
17–22 Sept
4.92 out of 5 average rating, 189 reviews
Guest favourite
Home in Chicago
New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage
7 bedrooms, 8 beds
12–17 Jul
4.85 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 85 reviews
Guest favourite
Flat in Chicago
Cozy Urban View Retreat Near Downtown - Sleeps 7
2 bedrooms, 4 beds
13–18 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Chicago
10 Min to Downtown | 3BR 2BA Spacious Home
3 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 3 reviews