What happens when a city tries—and fails—to sell a major airport three times?
Chicago’s Midway International Airport, the city’s second busiest, has been at the center of billion-dollar privatization attempts that collapsed spectacularly over two decades. From Mayor Richard M. Daley’s ambitious 2008 deal during the financial crisis to Rahm Emanuel’s 2013 attempt and Lori Lightfoot’s later refusal, Chicago has repeatedly failed to privatize Midway, costing taxpayers billions and leaving the airport stuck in time.

In this episode, we break down the political missteps, financial pitfalls, and consulting fees that turned Midway into the airport that never was. Discover why Chicago’s ambitions for privatization failed while other cities succeeded, how federal law and market conditions played a role, and what this means for the city’s infrastructure and finances today.

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