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Search results; Over 1,000 homes in Chicago

Superhost
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
1 bedroom, 1 bed, 1 private bathroom
12–17 Oct
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4.87 out of 5 average rating, 187 reviews
Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
Top guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
19–24 Oct
4.98 out of 5 average rating, 189 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
6–11 Dec
New place to stay
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Chicago
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
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
19–24 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
21–26 Sept
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
9–14 Nov
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Chicago
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 75 reviews
Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
27 Sept – 2 Oct
New place to stay