He was the third and youngest son of Thomas Chicheley, who appears in 1368 in still extant town records of Higham Ferrers as a suitor in the mayor's court, and in 1381-1382, and again in 1384-1385, was mayor: in fact, for a dozen years he and Henry Barton, school master of Higham Ferrers grammar school, and one Richard Brabazon, filled the mayoralty in turns.
His occupation does not appear; but his eldest son, William, is on the earliest extant list (1373) of the Grocers' Company, London.
The first recorded appearance of Henry Chicheley himself is at New College, Oxford, as Checheley, eighth among the undergraduate fellows, in July 1387, in the earliest extant hall-book, which contains weekly lists of those dining in Hall.
These monotonous writings, all in Dutch, flowed in a continual stream from 1524 (though none is extant before 1529) and amounted to over 200 in number.
His extant works are his Panegyrics on different emperors (in which he draws largely upon Statius, Ausonius and Claudian); and nine books of Letters and Poems, whose chief value consists in the light they shed on the political and literary history of the 5th century.