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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
Cozy, Artsy Gem in Historic Pullman
3 bedrooms, 3 beds, 1.5 private bathrooms
12–17 Oct
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4.95 out of 5 average rating, 120 reviews
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
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 30 reviews
Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
6–11 Dec
New place to stay
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
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 75 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
Top guest favourite
Flat in Chicago
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds
6–11 Jan
4.9 out of 5 average rating, 302 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
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 132 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, 15 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, 24 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, 28 reviews
Top guest favourite
Home in Chicago
Family Home in Bucktown | Parking | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.94 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
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Superhost
Guest suite in Chicago
Patio + FirePit • Park Free • Near Train & Dogs OK
2 bedrooms, 2 queen beds
3–8 Oct
New place to stay