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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Flat in Chicago
Hip Chicago Condo in fun shopping and dining area
2 bedrooms, 3 beds, 2 private bathrooms
16–21 Aug
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4.96 out of 5 average rating, 202 reviews
Top guest favourite
Flat in Chicago
Eclectic decor in Pilsen’s art district
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
Guest favourite
Home in Chicago
Spa tub and a private backyard fireplace
4.91 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Bungalow in Chicago
Game basement and fire pit in Beverly
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 18 beds, 3.5 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
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
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
Apartment in Chicago
Garden condo with a patio and grill
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
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
Home in Chicago
Spacious South Side home with EV charger
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
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
Bronzeville Hidden Oasis
4.98 out of 5 average rating, 183 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top 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
Top guest favourite
Home in Chicago
1908 coach house with rooftop skyline views
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
4.92 out of 5 average rating, 191 reviews, 3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Flat in Chicago
1888 cottage with an 85-inch TV
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept