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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
Apartment in Logan Square
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
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 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
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
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
Top guest favourite
Flat in Lake View
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 268 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, 67 reviews
Top guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 359 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Wicker Park
Spacious Studio w/Balcony in Bucktown/Wicker Park
2 beds, 1 bathroom
16–21 Nov
4.95 out of 5 average rating, 184 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
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, 121 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
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Studio Queen
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.89 out of 5 average rating, 9 reviews