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Search results; Over 1,000 homes in Chicago

Superhost
Loft in West Town
OHC Gorgeous Huge Studio Apt Steps to Blue Line
Studio, 3 beds, 1 private bathroom
2–7 Oct
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4.89 out of 5 average rating, 409 reviews
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Jan
4.96 out of 5 average rating, 84 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jan
4.95 out of 5 average rating, 132 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, 15 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3 bathrooms
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Flat in West Side
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
Guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
22–27 Oct
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds, 2 bathrooms
28 Nov – 3 Dec
4.98 out of 5 average rating, 91 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 962 reviews
Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 260 reviews