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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in West Loop
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Aug
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4.97 out of 5 average rating, 38 reviews
Superhost
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 126 reviews
Guest favourite
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.86 out of 5 average rating, 14 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 915 reviews
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
1–6 Mar
4.91 out of 5 average rating, 68 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 34 reviews
Guest favourite
Flat in Lake View
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 94 reviews
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 122 reviews
Guest favourite
Flat in Downtown Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 122 reviews
Guest favourite
Guest suite in Norwood Park
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 440 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Apartment in West Town
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Ravenswood
Bright family-friendly Lincoln Square 2-bed 1-bath
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 438 reviews