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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Uptown
Whole Flat in Private Club. Walk to L, Dining & Shows
1 bedroom, 1 bed, 1 shared bathroom
27 Sept – 2 Oct
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4.9 out of 5 average rating, 600 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 47 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
New place to stay
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 168 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Lincoln Park
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 reviews
Guest favourite
Flat in South Side
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Home in West Town
The Full House
4 bedrooms, 10 beds, 3.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 137 reviews
Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 112 reviews
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in The Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 147 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Flat in Bridgeport
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Ravenswood
Lincoln Square Gem!
2 bedrooms, 2 queen beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 505 reviews