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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Flat in Chicago
Kasa | Studio, Walk to Grant Park | South Loop
Studio, 1 bed, 1 private bathroom
30 Jul – 4 Aug
,
4.79 out of 5 average rating, 371 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
Guest favourite
Flat in Chicago
Newly renovated near Millennium Park
1 bedroom, 1 queen bed, 1 bathroom
22–27 Jul
4.97 out of 5 average rating, 93 reviews
Guest favourite
Flat in Chicago
Eclectic decor in Pilsen’s art district
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Home in Forest Park
Renovated 2 bedroom - 1.5 bath Coach House
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Aug
New place to stay
Top guest favourite
Flat in Chicago
Speakeasy-chic brownstone near Lake Michigan
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.94 out of 5 average rating, 16 reviews
Apartment in Chicago
Ukrainian Village 2 Bd/2ba - Steps from Division!
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Sept
4.98 out of 5 average rating, 62 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
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Spa bathroom and garden on tree-lined street
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Place to stay in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
4.9 out of 5 average rating, 48 reviews
Superhost
Flat in Chicago
Luxurious 5BD/2BA Duplex+Free Wine & Parking
5 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
New place to stay
Guest favourite
Flat in Chicago
Designer penthouse with views in Gold Coast
2 bedrooms, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Chicago
Sun-filled with private outdoor space
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 6 reviews