The land that makes up Streeterville was formed by a combination of natural and human forces. The construction of the pier at the mouth of the Chicago River in 1834 led to an accumulation of sand just north of it, creating an area of new land that became known as "The Sands." Much of the land to the north of “The Sands” filled in as a result of actions taken by George Streeter.

In 1886, Streeter, who went by Captain Streeter, ran his boat Reutan aground in Lake Michigan about four hundred feet offshore of Superior Street. Instead of vacating the sandbar, Streeter and his wife Maria took up residence in the boat and declared that their little island constituted the "District of Lake Michigan" and that the new territory was not subject to Chicago's laws. Sand accumulated around the Reutan and the Streeters allowed Chicagoans to dump building debris and other garbage near the boat, increasing the size of their island and closing the distance between it and Chicago's shore. Chicagoans along the shore mimicked this process, eventually filling in the gaps between the Streeters’ island and the city and claiming ownership to the made land.

The squatters living on the newly-constructed landfill created problems for the city. The city had also laid claim to the land-- some of which now houses part of Lake Shore Drive-- with an eye to future development. City officials who tried to police the district and enforce city alcohol and prostitution laws were often met with violence from the Streeters and residents of Streeterville.

Eventually the Streeters refloated their boat and used it to transport passengers in Chicago for the 1893 World's Fair. They continued to live in Streeterville, but were forced out again and again by Chicago police. The Streeters fought for their district in court, but ultimately lost, though the lawsuits over who owned the land continued until well after George Streeter's death in 1921.

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