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Search results; Over 1,000 homes in Chicago

Superhost
Guest suite in Norwood Park
Cozy Private Suite Near O'Hare & Downtown Chicago
1 bedroom, 1 bed, 1 private bathroom
27 Oct – 1 Nov
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4.77 out of 5 average rating, 371 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 32 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
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Jan
4.97 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Lincoln Park
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed, 1 bathroom
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, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 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
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, 34 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, 42 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
4.97 out of 5 average rating, 95 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 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
Top guest favourite
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Ukrainian Village
Beautiful Modern 1 bed/2bath West Town apartment
1 bedroom, 1 queen bed, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 23 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, 169 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
Top guest favourite
Flat in Edgewater
Modern 1 BR Near the L, Beach - Bright and Sunny!
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Downtown Chicago
Chic 2BR Gem with Fireplace
2 bedrooms, 2 beds, 2 bathrooms
15–20 Nov
4.98 out of 5 average rating, 165 reviews