33. Pullman Historic District

Location: 11141 South Cottage Grove Ave.
Website: pullmanil.org

An official Chicago Landmark, the Pullman District is the origin of the Pullman Company and factory, made famous for its “Pullman Sleeping Car.” The entire community was built expressly to house the factory's many employees (how's that for service?), the first of its kind in the country. Today it makes for one of Chicago's most unique neighborhoods. Feast your eyes on the decadent Hotel Florence (equipped with original furniture), or amble along with one of the many available walking tours.