early 15c., "ornamented with a checkered design," past-participle adjective from check (v.2).
"one who checks or controls," especially "one who collects money for others," 1867, agent noun from check (v.2).
also check-out, 1944, from the verbal phrase; see check (v.1) + out (adv.). Originally "training given to a pilot for using a specific aircraft;" the hotel sense of "administrative procedure followed when guests leave after a stay" is from 1958. Retail sense of "place where one pays for goods selected" is from 1947.
mid-14c., in chess, said of a king when it is in check and cannot escape it, from Old French eschec mat (Modern French échec et mat), which (with Spanish jaque y mate, Italian scacco-matto) is from Arabic shah mat "the king died" (see check (n.1)), which according to Barnhart is a misinterpretation of Persian mat "be astonished" as mata "to die," mat "he is dead." Hence Persian shah mat, if it is the ultimate source of the word, would be literally "the king is left helpless, the king is stumped."
mid-13c., "game of chess (or checkers);" c. 1300, "a chessboard, board with 64 squares for playing chess or similar games; a set of chessmen" (all now obsolete), a shortening of Old French eschequier "chessboard; a game of chess" (Modern French échiquier), from Medieval Latin scaccarium "chess-board" (see check (n.1)).
The meaning "pattern of squares" is from late 14c. That of "a man or piece in the game of checkers" is from 1864. British prefers chequer. From late 14c. as "a checked design." The word had earlier senses of "table covered with checked cloth for counting" (late 12c. in Anglo-Latin), a sense also in Old French (see checker (n.2)).