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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Logan Square
Private Suite w/ offstreet pkg, at Logan Sq Blu Ln
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.96 out of 5 average rating, 363 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
21–26 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
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 132 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 32 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
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
Top guest favourite
Flat in Lake View
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed
25–30 Oct
4.93 out of 5 average rating, 195 reviews
Top guest favourite
Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
2–7 Jan
4.97 out of 5 average rating, 86 reviews
Featured hotel
Hotel in Downtown Chicago
Junior two bedroom suite
2 bedrooms
18–23 Oct
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
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 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 North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Lincoln Park
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed
5–10 Dec
5.0 out of 5 average rating, 323 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
Superhost
Flat in West Side
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds
28 Sept – 3 Oct
New place to stay
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 Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds
3–8 Nov
4.96 out of 5 average rating, 143 reviews