The program, hosted by Orchard Drive, LLC, features a lineup of speakers including retired Southwest Airlines captain Louis Freeman, aerobatic pilot Douglas Byrd, and City of Chicago official Elgie Rena Neely. Keynote speaker Captain Barrington Irving, Jr., founder of The Flying Classroom, will lead the day’s discussions. The event focuses on small-group interactions, allowing students to engage directly with experts about the realities of the field.

Tom Flavin, president of Orchard Drive, emphasizes that the goal is to demystify complex career paths. By connecting aviation roles to familiar interests—such as sports, culinary arts, or animal care—the organizers aim to show students that the industry requires a diverse array of skill sets. This marks the fourth consecutive year the tour has partnered with Project H.O.O.D. in Woodlawn to provide mentorship and workforce development for local youth.