This may indeed shock you but according to the Streeterville Chamber of Commerce, the history of this now beautiful, high-end neighborhood is filled with land fraud, illegal construction waste dumping, gun battles and myriad trials. The history of Streeterville dates back to around 1886 when a man named George "Cap" Streeter and his wife, Maria were confirming the seaworthiness of their boat in Lake Michigan off of the Chicago shores. The couple originally planned to test the boat in the lake before heading to Honduras to become gunrunners. As it happens, plans changed and they decided to make a sandbar off of Michigan Avenue their home. According to Cap Streeter, a strong storm grounded their boat on said sandbar and instead of repairing and moving on, the husband and wife team decided to claim the sandbar as their property and live on the boat. There is some debate on the truth behind the storm claim as good weather was reported during the time surrounding Streeter's landing.

Per the Streeterville Chamber of Commerce:
"After the great Chicago Fire of 1871, the city was rapidly growing and developers were looking for a place to dump their construction waste. Although Streeter did not have the authority to do so, he charged developers to use the sandbar and surrounding area as a waste site. It quickly filled up with debris and Streeter started renting out the land, leading to the establishment of a shantytown. However, the wealthy landowners around "Streeterville" were worried that the shantytown would lower the property value of the area and fought to get rid of it."

In 1889, the Chicago Police attempted to forcibly remove Maria and Cap but were held off by gun play (remember the couple's original career path?) and the Streeters remained on their boat and surrounding land. Multiple law suites were filed by wealthy neighbors of "Streeterville", land developers Kellogg Fairbanks and Potter Palmer (of the famed Palmer House) continually battled while attempting to construct Lake Shore Drive and eventually removed Streeter and his pals from the land. However, after Palmer's death 1902, Streeter regained control of the land with an armed militia. Finally after days of fighting, the Chicago Police succeeded in permanently removing George "Cap" Streeter, Maria and their armed accomplices from the land.

It wasn't until the late 1920's when the Michigan Avenue Bridge was completed that the value of Streeterville real estate began to skyrocket. From that point on, Chicagoans and visitors alike see Streeterville as a stunning beauty and a gem in the crown of the city. Few know the sordid history behind Chicago's most luxurious neighborhood.