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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Penthouse Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
30 Sept – 5 Oct
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4.78 out of 5 average rating, 239 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 Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 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
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
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 30 reviews
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
New place to stay
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
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, 17 reviews
Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 75 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Chicago
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds, 2 bathrooms
6–11 Jan
4.9 out of 5 average rating, 302 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
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Top guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds, 1 bathroom
27 Nov – 2 Dec
4.95 out of 5 average rating, 197 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 32 reviews