First Airmail Letter Posted: December 9, 2018 Submitted by Gerard GuarinoNewark-Chicago-Newark Airmail Letter 1929.Joseph Cordasco, Grandfather to Gerard Guarino who submitted this scanned image, worked for the Post Office in 1929. It’s believed he mailed this letter to himself so that it would be delivered on the first airmail flight from Newark to Chicago and return to Newark. He wanted to document the flight.The timeline according to the stamps on the envelope (and on the enclosed letter) reads as follows: Newark received letter February 16, 1929 at 7:00 pm (envelope contains is a piece of paper with that date stamp on it)“First Airmail Flight”, Newark to Chicago, February 17, 1929 at 10:00 amChicago received letter February 17, 1929 at 9:30 pm.Chicago mailed letter to Newark February 18, 1929 at 4:00 am.Newark received letter February 18, 1929 at 9:00 pm. View the timeline of this first 1929 date-stamped letter delivered via airmail from Newark-Chicago-Newark