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Search results; Over 1,000 homes in Chicago

Top guest favourite
Loft in Wicker Park
Tea Studio in Wicker Park Spring Factory
2 bedrooms, 2 beds, 2 private bathrooms
23–28 Oct
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4.96 out of 5 average rating, 307 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
26–31 Oct
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds
25–30 Oct
4.98 out of 5 average rating, 253 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 959 reviews
Top guest favourite
Flat in Downtown Chicago
The Metropolitan Retreat (Fitness Center • Sauna)
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 122 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Flat in West Town
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds
1–6 Nov
4.9 out of 5 average rating, 300 reviews
Top guest favourite
Flat in Downtown Chicago
Highrise Hideout (Fitness Center • Sauna)
2 bedrooms, 3 beds
6–11 Sept
4.92 out of 5 average rating, 120 reviews
Top guest favourite
Apartment in West Town
Private rooftop | Breathtaking skyline view
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Flat in Lake View
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
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds
26–31 Oct
4.96 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds
8–13 Nov
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Ravenswood
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Apartment in Ravenswood
Lincoln Square Gem!
2 bedrooms, 2 queen beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 504 reviews