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(covers information from several alternate timelines)
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 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 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")