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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Grace House | Cozy, contemporary + convenient 2-BR
2 bedrooms, 2 beds, 1 private bathroom
17–22 Aug
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4.98 out of 5 average rating, 126 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
18–23 Aug
4.9 out of 5 average rating, 130 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds
16–21 Aug
New place to stay
Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
29 Aug – 3 Sept
4.91 out of 5 average rating, 276 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 441 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
17–22 Aug
4.75 out of 5 average rating, 16 reviews
Flat in Chicago
Bright & Cozy 1 Bdrm • Free Parking
1 bedroom, 2 beds
28 Sept – 3 Oct
4.57 out of 5 average rating, 58 reviews
Guest favourite
Room in Chicago
The Champlain Suite
1 bed
16–21 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
1–6 Nov
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Room in Chicago
En Suite Private Queen Bedroom/Bathroom
1 queen bed
30 Aug – 4 Sept
4.87 out of 5 average rating, 271 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
4–9 Oct
4.95 out of 5 average rating, 190 reviews
Superhost
Flat in Chicago
Luxury Penthouse Collection PH2 - Fulton Market
1 bedroom, 2 beds
7–13 Sept
New place to stay
Guest favourite
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed
1–6 Oct
4.96 out of 5 average rating, 94 reviews
Top guest favourite
Flat in Forest Park
Walk to Oak Park from Our Sunny Turn of the Century Apt
2 bedrooms, 3 beds
23–28 Oct
4.98 out of 5 average rating, 417 reviews