Chicago’s Billion-Dollar Miss: The Privatization of Midway Airport That Failed 3 Times episode artwork

EPISODE · Sep 19, 2025 · 11 MIN

Chicago’s Billion-Dollar Miss: The Privatization of Midway Airport That Failed 3 Times

from TrailMarkers By Expedition Money · host TrailMarkers By Expedition Money

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.▶ JOIN the Expedition Money Community for FREE!Use the code below at the following link ($1,200 value): https://expedition.money/subscription...Free Access Code: FREEXMYEAR▶ Get a copy of my book, AMAZING MONEY STORIES here! https://geni.us/R7efGET INSIDER COLLEGE PLANNING INFORMATION:▶ Mastering FAFSA Strategies to Maximize Your Financial Aid Course: https://www.udemy.com/course/collegef...----------GET MY BOOKS!▶ How I Make A Six-Figure Income On YouTube Book: https://geni.us/UZ2bnyd▶ How To Get Out Of Debt Fast Book: https://geni.us/HeWdQi1▶ Rethink Money Book: https://geni.us/O1tcs▶ Amazing Money Stories Book: https://geni.us/R7ef▶ Just The Essential Disney Hacks Book: https://geni.us/cYZO3T0▶ Living The Dream: 5 Strategies That Changed My Life Book: https://geni.us/dxPr▶ Discovering Travel Bliss: Insider Secrets for Transforming Ordinary Trips into Joyful Journeys Book: https://geni.us/QzzEgjo▶ Money Is Factscinating: Fascinating Money Facts, History, Stories & Trivia Book: https://geni.us/LckBTAX----------DISCOVER FINANCIAL INDEPENDENCE:▶ Podcast: https://geni.us/N79P5UC----------FOLLOW ON SOCIAL MEDIA:▶ Instagram:   / expedition.money  ▶ Facebook:   / expeditionmoney  ▶ X:   / expeditionmoney  ▶ LinkedIn:   / expeditionmoney  

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Chicago’s Billion-Dollar Miss: The Privatization of Midway Airport That Failed 3 Times

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