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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Lincoln Park
Sophisticated Flat in Historic Building
1 bedroom, 1 bed, 1 private bathroom
6–11 Nov
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4.96 out of 5 average rating, 500 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
21–26 Oct
Featured hotel
Rooms in Downtown Chicago
Junior two bedroom suite
2 bedrooms
27 Sept – 2 Oct
Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds
23–28 Sept
4.92 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
9–14 Jan
4.96 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 60 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 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
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
2–7 Nov
4.92 out of 5 average rating, 75 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
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
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 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
Top guest favourite
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 169 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
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