Craig O'Mara didn't start out intending to be a pilot. He was a bird-watcher, and became more interested in flight as he watched the birds, and started flying as a teenager. He soloed as a 16-year old, and received his Private Pilot certificate on his 17th birthday.

In 1979 he joined the Air Force Reserves as a C-9 pilot, flying air ambulance missions all over the United States, as well as overseas. He flew the C-9 for a total of 20 years.

In 1985 he was hired by United Airlines, and served on the DC-10, B737, B757/767, B747 and B787. He was a Line Check Airman on many of these aircraft.

In addition to his United flying, Craig flew as a pilot for NASA in the B747SP. He also flew a variety of warbirds.