mid-15c., "talk idly, babble," short for chatter (v.). Meaning "to converse familiarly" is from 1550s. Sense of "flirt with, ingratiate oneself with" (later often with up (adv.)) is from 1898. Related: Chatted; chatting.
chat (n.)
1520s, "chatter, frivolous talk;" see chat (v.). Meaning "familiar conversation" is from 1570s. As a name for birds with chattering cries, 1690s. Chat show for what in U.S. is a talk show is attested from 1967. Chat room in the online sense is attested by 1994, from the days when AOL ruled the World Wide Web.
chasten
chastise
chastisement
chastity
chasuble
chat
chateau
Chateaubriand
chatelaine
chatoyant
Chattahoochee