Though not known for certain, Pioneer Court is believed to be the location of Jean Baptiste Point DuSable and wife Catherine's home site. DuSable is generally credited with being the first non-native, permanent settler of Chicago.   

DuSable's background is representative of the multicultural and fluid nature of the Great Lakes region at that time. He was born somewhere in French North America in the mid eighteenth century and spent time at British and French held trading posts in Detroit, Michigan City, and Fort Michilimackinac before making his way to Chicago. In 1788, DuSable married a Potawatomi woman named Catherine in a Roman Catholic ceremony in Peoria, Illinois, though they had probably been living together as a married couple for several years.  

Around the same time, the DuSables established a homestead near the mouth of the Chicago River. DuSable sold his property and moved to St. Charles, Missouri after his wife died, sometime before or during 1800. He remained in St. Charles, which was under Spanish control at the time, until his death in 1818.   

The DuSable home site is also the location of John Kinzie's Chicago residence. Kinzie, another early settler, moved onto the DuSable property in 1804. Kinzie, like DuSable, had connections with Native Americans, British, and French traders across the Great Lakes region. His wife Eleanor was taken captive as a child and raised by the Seneca and Kinzie had spent time living among Potawatomi. Kinzie's family owned the land until 1834.  

The plaza was built in 1965 and the Du Sable home site was designated a National Historic Landmark in 1976. The city's Museum of Negro History and Art was renamed the DuSable Museum in 1973 in honor of DuSable, who was of Afro-French heritage. The bridge spanning Michigan Avenue is also named after DuSable.