Du Sable built his first house in the 1770s, thirty years before Fort Dearborn was established on the banks of the Chicago River. By the time he sold to Kinzie's frontman, Jean LeLime, his property included a house, two barns, a horsemill, a bakehouse, a poultry house, a dairy and a smokehouse. The interior was richly appointed as well.
Du Sable married the daughter of one of the local Potawatomi chiefs. During the Revolutionary War, he was imprisoned briefly by the British at Detroit, Michigan.