The following summary is based largely on "A Chaucer Chronology" in John H. Fisher's Complete Poetry and Prose of Geoffrey Chaucer, 2nd edition, with some minor additions and abbreviations of my own. Records of plague outbreaks are taken from Singman and McLean's Daily Life in Chaucer's England. For more information, see "Chaucer in His Time," in pp. 956-960 of Fisher, which covers the material in greater detail, and a list of biographies at the bottom of this page. Text in black refers to general historical events. Text in red refers to events specific to Chaucer's life. Text in purple refers to Chaucer's writings. A more complete list of events for the years 1300-1400 can be found here.
Some Select Chaucer Biographies:
Baugh, Albert C. "Chaucer the Man." In Companion to Chaucer Studies. Ed. Beryl Rowland. rev. ed. NY: Oxford UP, 1979.
Brewer, Derek. Chaucer and His World. NY: Dodd, Mead, 1977.
Crow, Martin M., and Clair C. Olson, eds. Chaucer Life-Records From Materials Compiled by John M. Manly and Edith Rickert, with the Assistance of Lilian J. Redstone and Others. Oxford, Clarendon 1966.
Gardner, John Champlin. The Life and Times of Chaucer. NY: Knopf, 1976. (Use with caution!)
Howard, Donald R. Chaucer: His Life, His World, His Works. NY: Dutton, 1987.
Hulbert, James R. Chaucer's Official Life. Menasha, WI, 1912.
Kern, Alfred. The Ancestry of Chaucer. Baltimore, MD, 1906.