Iotian society was based on the organization of the gangs of the Chicago of the 1920s because of cultural contamination through the book Chicago Mobs of the Twenties
Chicago was a city on the North American continent on Earth, in the state of Illinois, within the borders of the United States of America. During the fledgling days of Major League Baseball, Chicago was the home of the Chicago Cubs baseball team. (DS9: "Emissary") During the early 20th century it was also the location of the Palace Theater. (VOY: "Repression")
In the 1920s, gangs of outlaws and organized crime had almost taken over Old Chicago. A book was written about the ordeal in 1992, titled Chicago Mobs of the Twenties. A copy of this book found its way to Sigma Iotia II in the 2160s. (TOS: "A Piece of the Action")
In the mid-20th century, people, even those in rural areas, could hear about what was happening in this city on the radio. Though people might feel they were far from events, radio brought them in closer. (TNG: "The Big Goodbye")
In 2045, Kiki Morris Raymond was born in this city. (TNG: "The Neutral Zone")
In the late 21st century, Janice Lee Raymond was born in this city. (TNG: "The Neutral Zone"
While playing out a Dixon Hill simulation on the holodeck, Jean-Luc Picard spontaneously made up an alias for William Riker, saying that he was "Nails" from Chicago. (TNG: "Manhunt")
In 2375, the duplicate of Tom Paris created by the Silver Blood of the Demon planet wanted to take his new wife, the duplicate B'Elanna Torres, to 1928 Chicago on a holodeck honeymoon. Although the duplicate Neelix thought it was an uninteresting choice, Paris created the holo-program and the newlyweds planned a week-long stay at Graystone Hotel, driving up Michigan Avenue in a vintage Duesenberg, hobnobbing with the stars of the silver screen, and dancing the Charleston at a genuine speakeasy called the Green Mill. Unfortunately, Torres' cellular structure degraded after exposure to an enhanced warp drive installed aboard the duplicate USS Voyager, and the couple never made the trip. (VOY: "Course: Oblivion")