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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Chicago
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 private bathrooms
10–15 Aug
,
5.0 out of 5 average rating, 60 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
Guest favourite
Flat in Chicago
Newly renovated near Millennium Park
4.97 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
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
12–17 Oct
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 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
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Guest favourite
Flat in Chicago
Open-concept flat with a private patio
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
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
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
Renovated with free parking near Blue Line
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in Chicago
Open-concept home 10 minutes from O’Hare
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Sept
Place to stay in Chicago
Guest room in Dunning, Chicago IL
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Sept
Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
4.89 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Superhost
Flat in Chicago
Duplex with a jacuzzi and Peloton
New place to stay, 5 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Guest favourite
Place to stay in Chicago
12 minutes from O’Hare with free parking
4.9 out of 5 average rating, 48 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct