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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
,
4.96 out of 5 average rating, 202 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
LIVN Millennium Park Downtown Chicago 1 BR
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
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
Top guest favourite
Flat in Chicago
Speakeasy-chic brownstone near Lake Michigan
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 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
Sunlit mid-century brick ranch, tree-lined street
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
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
2BR Avondale Apt: Free Parking + Steps to Blueline
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
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
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 48 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Oct
Top guest favourite
Flat in Chicago
Spa bathroom and garden on tree-lined street
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Place to stay in Chicago
Halfway between O’Hare and downtown
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Sept
Superhost
Flat in Chicago
Luxurious 5BD/2BA Duplex+Free Wine & Parking
New place to stay, 5 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 54 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Nov
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
20–25 Sept
Top guest favourite
Flat in Chicago
Chic 3BR Sun-Filled Oasis: Wicker & Logan Square
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug