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This was the Chicago North Shore & Milwaukee Railroad (the "North Shore Line"). Founded in 1895 as a single-tracked streetcar line in Waukegan, Illinois, over the next 20 years it expanded into a double-tracked, high-speed line between Chicago and Milwaukee. In 1916 it was acquired by Samuel Insull, an Anglo-American electrical tycoon who owned Commonwealth Edison (ComEd), the Chicago "L" and a handful of other electric railroads.
Insull basically transformed the North Shore into the standard-bearer of the interurban industry. In addition to running trains directly into the Chicago Loop over the "L" system, he instituted things like full-dining car service, named "limited" trains, direct connections to steam railroads, airlines and lake ferries. For a brief period of time in the 1920s, the North Shore was the fastest electric railroad in the world, and remained the fastest interurban line until its abandonment. In 1941, they became the first interurban to introduce a streamliner service - the "Electroliner" - air-conditioned, articulated and capable of 110mph speeds.
The North Shore Line was the final interurban line to be abandoned, surviving all the way until 1963 (its life was prolonged by a legal battle between the owners and the commuters). A tiny portion of the route was acquired by the Chicago Transit Authority and converted into the "Skokie Swift" (Renamed the "Yellow Line" in 1993, it still utilized the North Shore's overhead wires for power until 2004).