Earlier this month, Amazon CEO Jeff Bezos announced that the Seattle-based company is on the hunt for another U.S. city to be home to a second Amazon head office. Whichever city lands the coveted headquarters will likely see major economic benefits, as the company promises to bring with it 50,000 jobs. While Chicago has proven it has what it takes to be a successful HQ base—the city and suburbs are already home to Boeing, SunCoke Energy, and United Airlines—it also poses some deal-losing factors that may turn away Amazon.

Morning Shift talks to John Pletz, senior reporter covering technology and venture capital at Crain’s Chicago Business.