Drexel Boulevard was named after Philadelphia banker Francis M. Drexel, who acquired the land through a 1840s real estate foreclosure. Ironically, Drexel never resided in Chicago and it is unclear if he ever visited the city.
Although Drexel Boulevard had been partially laid out prior to the Great Chicago Fire of 1871, no planting or ornamental work had begun and the fire put the boulevard project on hold. It was not until 1872 that work resumed on Drexel, when a new landscape architect was hired. Under the direction of H.W.S. Cleveland, 500 trees were planted along Drexel and Grand Boulevards. The one-and-a-half-mile Drexel Boulevard became the hidden gem of the boulevard system.