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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Stylish First Flr. Studio. Best Location Division+Hermitage.
1 bedroom, 1 bed, 1 private bathroom
29 Aug – 3 Sept
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4.97 out of 5 average rating, 304 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago
Easy Downtown Access from Cozy Pilsen Nest
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
New place to stay, 5 bedrooms, 7 beds, 3.5 bathrooms
9–14 Aug
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 bathrooms
6–11 Jul
Top guest favourite
Home in Chicago
Historic Spacious Chicago Home • Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4.98 out of 5 average rating, 183 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
4.92 out of 5 average rating, 189 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Flat in Chicago
Stylish & Spacious Multi-Level Apt in Wicker Park
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 433 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Chicago
New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage
4.85 out of 5 average rating, 33 reviews, 7 bedrooms, 8 beds, 3 bathrooms
12–17 Jul
Superhost
Flat in Chicago
Paradise Lounge South loop 3br W/ Balcony
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
4.97 out of 5 average rating, 156 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
Top guest favourite
Flat in Oak Park
Spacious & Stylish Duplex Near Downtown w/Parking
5.0 out of 5 average rating, 85 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
5.0 out of 5 average rating, 18 reviews, 4 bedrooms, 4 beds, 3 bathrooms
6–11 Jul
Top guest favourite
Flat in Chicago
NorthSide Chicago duplex 5-BD,2King size-free park
4.97 out of 5 average rating, 198 reviews, 5 bedrooms, 6 beds, 2 bathrooms
8–13 Nov