Trained in law at an early age by Andrew Hamilton, Chew inherited his mentor's clients, the descendants of William Penn, including Thomas Penn (1702–1775) and his brother Richard Penn Sr. (1706–1771), and their sons, Governor John Penn (1729–1795), Richard Penn Jr. (1734–1811), and John Penn (1760–1834). The Penn family was the basis of his private practice, and he represented them for six decades.
Chew had a lifelong personal friendship with George Washington, who is said to have treated Chew's children "as if they were his own." Chew lived and practiced law in Center City Philadelphia four blocks from the Pennsylvania State House, later renamed Independence Hall, and provided pro bono legal counsel on substantive law to America's Founding Fathers during their creation of the United States Constitution and Bill of Rights.
Benjamin Chew was the son of Samuel Chew, a physician and first Chief Justice of Delaware, and Mary Galloway Chew (1697–1734). He was born in Anne Arundel County, Maryland, at his father's plantation, Maidstone. Benjamin Chew's great-great-grandfather, John Chew (1587–1668), a successful merchant, arrived in Jamestown in 1622 on the ship Charitie; he was granted 1,600 acres (6.5 km2) of land in York County, Virginia.

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