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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Guest favourite
Flat in Chicago
Cozy Bedroom in Wrigleyville (Entire Apt)
1 bedroom, 2 beds, 1 private bathroom
19–24 Oct
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4.77 out of 5 average rating, 261 reviews
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
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
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
12–17 Oct
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
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
Apartment in Chicago
Garden condo with a patio and grill
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
22–27 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
Place to stay in Chicago
Central spot near downtown with workspace
New place to stay, 1 bedroom, 1 bed, 2 bathrooms
13–18 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
29 Aug – 3 Sept
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 Berwyn
Remodeled with a backyard game room
4.91 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Chicago
Free parking and a home gym
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
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
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
Home in Chicago
Evergreen Park 4 bd/3 BA w/Theater, Gym, & Parking
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 5 beds, 3.5 bathrooms
21–26 Sept
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept