This plaza marks the location of Wolf Point, an important meeting ground at the confluence of the north and south branches of the Chicago River. The branches came together at Wolf Point, also known as the "Forks", and then ran east into Lake Michigan.

Early non-native settlers opened inns and taverns at Wolf Point, providing food, lodging, and entertainment to the many English, French, and Native American people who used the area as a middle ground on which to trade and establish relationships. Samuel and John Miller opened the Miller House inn here in 1827 and Chicago's first river ferry service in 1829. Samuel married Elizabeth Kinzie, daughter of John and Margaret Kinzie, who were among Chicago's earliest non-native settlers. Elizabeth's brother James opened the Wolf Point Tavern in 1829 and the Green Tree Tavern in 1833.

Early Chicagoans built up the area around Wolf Point as well. Mark and Monique Beaubien's Sauganash Hotel, Chicago's first frame building, was located across the Chicago River from Wolf Point, near what is now the intersection of Wacker Drive and Lake Street. The Beaubiens operated a ferry service across the river and were generally well-liked among early settlers for the entertainment they provided at their hotel. Beaubian's brother John also lived on the south bank of the river. The Sauganash was the location where residents voted to incorporate as a town (they would incorporate as a city in 1837). The hotel burned down in 1851. The Wigwam, a convention center, was built on the site and later hosted the 1860 Republican National Convention. The site of the Sauganash Hotel and the Wigwam was designated a Chicago landmark in 2002.

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