Our Story

Founded in 2023, Ross Air Chicago was built on a legacy that spans more than seventy years and three generations of aviators. For founder Jacob Ross, aviation isn’t just a career — it’s a continuation of his family’s lifelong dedication to flight.

Jacob’s grandfather, Howard Ross, served as a Navy Fighter Pilot during World War II, flying with honor and precision. After the war, he devoted himself to preserving aviation history, building a collection of vintage warbirds and sharing his passion with others. But beyond his aircraft, what truly defined him was his commitment to education — helping others become safe, confident, and capable pilots who respected the craft as much as he did.

Growing up in that environment, Jacob was surrounded by the hum of engines, the smell of avgas, and the stories of courage and mentorship that shaped his family’s legacy. Those experiences instilled in him not only a love for flying but also a responsibility to carry that mission forward.

That calling became the foundation for Ross Air Chicago — a flight training organization created to honor his grandfather’s values while preparing the next generation of aviators. Every flight lesson, every discovery flight, and every student reflects that same dedication to safety, confidence, and passion for aviation.

From its home base at Waukegan National Airport (KUGN), Ross Air Chicago blends classic inspiration with modern instruction, helping pilots of all levels write their own chapter in a legacy built on excellence and love of flight.

Ross Air Chicago — continuing a family mission to inspire, educate, and elevate.

LCDR Howard Ross USN (Ret) with his T-34 Mentor (left) and his P-51 Mustang Glamorous Gal (right).