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Search results; Over 1,000 homes in Chicago

Superhost
Hotel room in Chicago
Luxurious King Room in Boutique Wicker Park B&B
1 bedroom, 1 bed, 2 private bathrooms
23–28 Oct
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4.75 out of 5 average rating, 4 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
23–28 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.-5
1 double bed
6–11 Sept
New place to stay
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
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
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
Flat in Chicago
Guest Favorite Newly Renovated 1BR Near Lakeview
1 bedroom, 1 queen bed
1–6 Oct
4.95 out of 5 average rating, 96 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
Top guest favourite
Flat in Oak Park
Big & Bright Treetop Oasis Near Downtown w/Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 95 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
Guest favourite
Room in Chicago
The Champlain Suite
1 bed
8–13 Sept
4.95 out of 5 average rating, 41 reviews
Guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
8–13 Nov
4.95 out of 5 average rating, 190 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed
31 Oct – 5 Nov
4.95 out of 5 average rating, 120 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds
17–22 Aug
4.71 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
16–21 Feb
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chicago
West Loop 2BR : Skyline Views + Prime Location
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 69 reviews
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 22 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