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Search results; Over 1,000 homes in Chicago

Top guest favourite
Bungalow in Chicago
Chicago Bootlegger House Sleeps 10-20
6 bedrooms, 10 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.96 out of 5 average rating, 159 reviews
Superhost
Apartment in Chicago
Elegant Historic Duplex | Old Town • Lincoln Park
2 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
New place to stay
Superhost
Home in Schaumburg
Chicagoland-Schaumburg/ORD 3BR Ranch Home, sleeps7
3 bedrooms, 4 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 4 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, 118 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.92 out of 5 average rating, 72 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed, 1 bathroom
12–17 Aug
4.96 out of 5 average rating, 112 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guest suite in Chicago
Peaceful Portage Park Apartment
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.94 out of 5 average rating, 464 reviews
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Superhost
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
6–12 Jul
New place to stay
Top guest favourite
Flat in Chicago
Easy Downtown Access from The Pilsen Haven
3 bedrooms, 3 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chicago
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 8 reviews
Flat in Berwyn
Spacious 2BD w/Game Table for 7 near City+Airport
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
New place to stay
Top guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 101 reviews
Top guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.98 out of 5 average rating, 184 reviews
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
26–31 Jul
New place to stay