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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Fulton Market Loft | Rooftop Fire Pit | Parking
3 bedrooms, 3 beds, 2.5 private bathrooms
25–30 Sept
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4.96 out of 5 average rating, 288 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 35 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 47 reviews
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, 14 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds
17–22 Oct
4.94 out of 5 average rating, 497 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, 22 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 522 reviews
Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 111 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, 79 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
6–11 Sept
New place to stay
Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 112 reviews