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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Stylish 2BR stunner w/ unbeatable location
2 bedrooms, 3 beds, 1 private bathroom
5–10 Oct
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4.92 out of 5 average rating, 206 reviews
Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
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
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 101 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
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, 24 reviews
Guest favourite
Flat in Chicago
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
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.92 out of 5 average rating, 211 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
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
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, 9 reviews
Top guest favourite
Flat in Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds, 6 bathrooms
8–13 Nov
5.0 out of 5 average rating, 17 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
Top guest favourite
Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 924 reviews
Top guest favourite
Home in Chicago
Family Home in Bucktown | Parking | Walk to Train
5 bedrooms, 5 king beds, 3.5 bathrooms
24–29 Sept
4.94 out of 5 average rating, 16 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