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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Roscoe Village
The Roscoe Village Guesthouse
2 bedrooms, 2 beds, 1 private bathroom
25–30 Oct
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4.91 out of 5 average rating, 212 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
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 35 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
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
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, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 32 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, 961 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
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 108 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, 14 reviews
Top guest favourite
Flat in Wicker Park
【Central】- Eclectic Fun 1BR APT in Wicker Park
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 165 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, 40 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
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
22–27 Oct
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Wicker Park
CHIC DOWNTOWN PENTHOUSE w/ private roof +parking
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.93 out of 5 average rating, 226 reviews
Top guest favourite
Apartment in Lincoln Park
1750 sq. ft. Pets OK | full Kitchen | Workspace
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Room in Downtown Chicago
Deluxe King Room · Juliette Balcony · Sono B&B
1 king bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.95 out of 5 average rating, 111 reviews
Top 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