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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Wrigleyville
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 287 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
Home in Lincoln Park
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
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
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 North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 39 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
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, 960 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
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 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 Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 83 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 167 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 Ravenswood
Lincoln Square Gem!
2 bedrooms, 2 queen beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 504 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
Apartment in Wicker Park
CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
2 bedrooms, 3 beds
26–31 Oct
4.93 out of 5 average rating, 225 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