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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
2 bedrooms, 3 beds, 2.5 private bathrooms
12–17 Oct
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4.96 out of 5 average rating, 185 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
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
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
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
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
6–11 Dec
New place to stay
Guest favourite
Flat in Chicago
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 Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 24 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, 7 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
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chicago
Explore•Relax | Family/Pets | 10m O’Hare | 30m DT
7 bedrooms, 13 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 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
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
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
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
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
3–8 Nov
4.95 out of 5 average rating, 111 reviews
Guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
2–7 Nov
5.0 out of 5 average rating, 36 reviews