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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
Modern vintage chic steps from Wrigley: park free
3 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.96 out of 5 average rating, 271 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 121 reviews
Guest favourite
Home in Chicago
Spa tub and a private backyard fireplace
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Bungalow in Chicago
Game basement and fire pit in Beverly
5 bedrooms, 18 beds, 3.5 bathrooms
2–7 Aug
4.95 out of 5 average rating, 41 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 81 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 13 reviews
Apartment in Chicago
Garden condo with a patio and grill
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen flat with a patio and fireplace
2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
4.94 out of 5 average rating, 66 reviews
Home in Chicago
Spacious South Side home with EV charger
3 bedrooms, 3 queen beds, 1 bathroom
19–24 Jul
New place to stay
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
Roomy and Comfortable Apartment with everything UN
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Apartment in Chicago
Entire building with 3 private units
9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 75 reviews
Guest favourite
Flat in Chicago
Spacious garden apartment in Bronzeville
4 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 183 reviews
Guest favourite
Flat in Chicago
Open-concept flat with a private patio
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Double-height windows in a Pilsen duplex
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
1888 cottage with an 85-inch TV
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 65 reviews
Guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.92 out of 5 average rating, 191 reviews