An amateur pilot, Whitfield owned a small red and silver Taylor Cub airplane which he occasionally flew (mostly for recreation).

Whitfield departed Roosevelt Field in Mineola in his small silver and red Taylor Cub monoplane, which he planned to land at an airfield in Brentwood, New York (approximately 22 miles (35 km) away).

An investigation discovered that on the day he vanished Whitfield had checked into a hotel in Garden City on Long Island under an alias he occasionally employed: "Albert C. White".

When the hotel room was searched, it was discovered that his personal belongings (including his passport), clothing, cuff links engraved with his initials, two life insurance policies (in his name listing his wife, Elizabeth Halsey Whitfield, as the beneficiary), and several stock and bond certificates made out in Andrew's and Elizabeth's names, were all left behind in the hotel room.

Whitfield had married the former Elizabeth Halsey earlier that year and had been planning to move to Bethlehem, Pennsylvania, (with his new wife) the same month that he disappeared.