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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Ravenswood
Private suite in Lincoln Square
1 bedroom, 1 bed, 1 shared bathroom
18–23 Oct
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4.97 out of 5 average rating, 484 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
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
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
15–20 Nov
5.0 out of 5 average rating, 62 reviews
Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
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
26–31 Oct
4.96 out of 5 average rating, 143 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, 109 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Guest favourite
Flat in Downtown Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 14 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 West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds
28 Nov – 3 Dec
4.98 out of 5 average rating, 91 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed
29 Nov – 4 Dec
4.97 out of 5 average rating, 924 reviews
Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 260 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
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, 962 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, 44 reviews
Top guest favourite
Flat in Ukrainian Village
Beautiful Modern 1 bed/2bath West Town apartment
1 bedroom, 1 queen bed
9–14 Nov
5.0 out of 5 average rating, 23 reviews
Guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Flat in West Side
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
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