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Multiple realities
(covers information from several alternate timelines)
Gangsters with heaters

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 in Illinois. This city was located on the coastline of a lake. (TOS: "A Piece of the Action"; TNG-R: "The Neutral Zone", okudagram; ENT: "Storm Front", "Storm Front, Part II")

During the fledgling days of Major League Baseball, Chicago was the home of the Chicago Cubs baseball team. (DS9: "Emissary")

In the 1920s, with the city government in near collapse, organized crime had almost taken over Chicago. A book was written about the crisis 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 1932, the Palace Theater, a movie house, was built in this city. (VOY: "Repression")

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")

The pages seen in the episode were actually from the detective novel, The Listening Man, by author John A. Moroso. This novel was published in 1924. Information on Chicago was from page 110.

In an alternate timeline in which Nazi Germany had invaded the United States, as of 1944 Chicago was controlled by American forces. (ENT: "Storm Front", "Storm Front, Part II")

In 2045, Kiki Morris Raymond was born in this city. (TNG-R: "The Neutral Zone", okudagram)

In 2071, Janice Lee Raymond was born in this city. (TNG-R: "The Neutral Zone", okudagram)

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")

In "The Neutral Zone", the use of this city as a birthplace came from the remastered Clare Raymond family tree.
This city was named on a German map of the United States (Die Vereinigten Staaten von Amerika) in "Storm Front". Its location was represented by an orange circle. In most states the orange circles marked the state capitals, while in Illinois both Chicago and the actual capital Springfield were marked such.
In the final draft script of "Carpenter Street", Charles Tucker III cited Chicago as one of a mere few cities in the United States of America which had a football team, the Chicago Bears, and a baseball team, the Chicago Cubs, that had "matching names", other such cities being Detroit and New York City.

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