The Cleveland lakefront airport, Burke, was originally kept busy by the Fed bank branch downtown. When checks were prevalent, they needed the close access to an airport for getting them out in a timely manner. Time was money. Now with ACH and electronic payments, the Fed doesn't need the airport like they did and traffic has dropped off.
Not sure what Chicago's Fed did or if there is anything similar in Toronto, but could that be a reason why these cities have these airports and similar places like Detroit, Buffalo and Milwaukee do not?
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