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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Chicago
Charming private coach house
1 bedroom, 2 beds, 1 private bathroom
5–10 Aug
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4.97 out of 5 average rating, 60 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
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
2–7 Aug
Home in Forest Park
Renovated coach house near downtown
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Flat in Chicago
Minimal duplex with free private parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Apartment in Chicago
Modern Woodlawn condo near UChicago
4.96 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Fireplace and patio near UChicago
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Home in Chicago
Spacious South Side home with EV charger
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Apartment in Chicago
Entire building with 3 private units
4.8 out of 5 average rating, 10 reviews, 9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
4.91 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
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
18–23 Aug
Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4.94 out of 5 average rating, 141 reviews, 4 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Top guest favourite
Flat in Chicago
Massive roof deck in Bronzeville
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Flat in Chicago
Spacious garden apartment in Bronzeville
4.98 out of 5 average rating, 183 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Guest favourite
Flat in Chicago
Designer loft with views in Gold Coast
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
4.88 out of 5 average rating, 434 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Aug