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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Chic 2BR Gem with Fireplace
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Nov
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4.98 out of 5 average rating, 164 reviews
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
24–29 Oct
New place to stay
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
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
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.89 out of 5 average rating, 81 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
21–26 Sept
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 36 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, 23 reviews
Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
16–21 Oct
4.88 out of 5 average rating, 447 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 6 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
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 reviews
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
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
20–25 Sept
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds
8–13 Nov
5.0 out of 5 average rating, 17 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, 27 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews