Due to his outstanding abilities at school, Henry was introduced to William of Wykeham, Bishop of Winchester, who was working in the Castle on plans for the building of New College, Oxford. He accompanied the Bishop to Winchester to continue his studies,then laterly at New College where he stayed until 1392. He moved to London to practise in the ecclesiastical courts where his rise was rapid. Like other ecclesiastical laywers he was paid with ecclesiastical preferments. This led eventually to his appointment in 1402 to the Archdeaconry of Salisbury, then Chancellor of Salisbury. His further appointment was to the Bishopric of St. David's, and in 1414 he became Archbishop of Canterbury.
He was certainly at the Battle of Agincourt with Henry V and there was a charge, versified by Shakespeare (Henry V. act 1, sc.2) from Halls Chronicle, of having tempted Henry V into the conquest of France for the sake of diverting parliament from the disendowment of the Church.
Chichele was present at the siege of Rouen, and the King committed to him the negotiations for the surrender of the city in 1419 and for the marriage of Katherine. He crowned Katherine at Westminster in February 1421 and in December of the same year baptised her child, Henry VI.
He founded at least three colleges, one at Higham Ferrers and two at Oxford. The licence for the first was given by Henry V in May 1422 and was closely modeled on Winchester College, and to it was attached an alms-house for 12 poor men (more of the Bede House later).
He retained the position of Archbishop of Canterbury until his death in 1443, at the age of 81 years. He was the longest serving Archbishop of Canterbury. His tomb is located within Canterbury Cathedral.
The College, The Grammar School and the Bede House were all founded by Chichele in the fifteenth century.