filters

Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Chicago
1 GB Wi-Fi, 1 Reserved Parking Space, Sleeps 4
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept
,
4.85 out of 5 average rating, 54 reviews
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
24–29 Oct
New place to stay
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds, 2 bathrooms
22–27 Oct
4.89 out of 5 average rating, 80 reviews
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
19–24 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 36 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
9–14 Sept
4.33 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chicago
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 Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds, 2.5 bathrooms
8–13 Nov
4.98 out of 5 average rating, 63 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 110 reviews
Guest favourite
Flat in Chicago
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
Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 27 reviews
Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds, 6 bathrooms
20–25 Sept
4.8 out of 5 average rating, 10 reviews
Superhost
Flat in Chicago
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 60 reviews