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Search results; Over 1,000 homes in Chicago

Superhost
Apartment in Chicago
Private hot tub - King bed suite - Free parking
Studio, 1 bed, 1 private bathroom
12–17 Oct
,
4.93 out of 5 average rating, 281 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed, Parking, Deck, Yard
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 99 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 59 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 207 reviews
Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
6–11 Sept
New place to stay
Top guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
12–17 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 32 reviews
Superhost
Flat in Chicago
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews