The building was built atop the site of a cabin belonging to Chicago's first permanent resident, Jean Baptiste Pointe du Sable.

The site was originally settled by du Sable around 1779, and operated as a personal residence and fur-trading post, forming the very beginnings of the city of Chicago.

In 1803, Fort Dearborn was built by the United States government immediately across the river, helping to protect the growing trading post from local Native American tribes.

Even as Michigan Avenue was slowly rebuilt into the city's premier street beginning in the 1920s, the site remained industrial in usage, and by 1961, it had become a parking lot.

In 2017 the riverfront restaurant and helical staircase were replaced by a new flagship store for Apple, also with the address 401 N Michigan Ave, and designed by the London-based architecture firm Foster + Partners.

In 1992, Pioneer Court was redesigned and extended eastward around the office tower by Cooper, Robertson & Partners in a vaguely Postmodernist style, in conjunction with the massive Cityfront Center development just to the east.