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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Town
Your perfect place looks like?
3 bedrooms, 3 beds, 2 private bathrooms
18–23 Oct
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4.93 out of 5 average rating, 178 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
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 Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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 North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds
6–11 Sept
New place to stay
Top guest favourite
Flat in Uptown
Private studio near Wrigley
1 bedroom, 2 beds
29 Nov – 4 Dec
4.93 out of 5 average rating, 154 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
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
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
25–30 Oct
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
23–28 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 27 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
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 312 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