George Chesterton joined the Royal Air Force the week he left school in July 1941, and after early training (during which he ate his meals in London Zoo and had a medical examination in the Long Room at Lord's) he spent a year learning to fly in Canada. Having gained his Wings he returned to England, but not before he spent a leave in New York where he danced with Katherine Hepburn.

The main part of his flying career was spent flying Stirlings and included taking part in the D-Day offensive and operation Market Garden, as well as Special Operations Executive flights over Europe. The final days after the war were spent playing cricket for the Air Force.

After the war George Chesterton went up to Oxford where he earned an MA as well as a Cricket Blue. He subsequently played cricket for Worcestershire and became a School Master at Malvern College.