Online Etymology Dictionary

cheapskate (n.): also cheap skate, "miserly person," 1896, from cheap (adj.), second element perhaps from American English slang skate "worn-out horse" (1894), of uncertain origin.
chear: obsolete spelling of cheer (n.).
cheat (v.): mid-15c., "to escheat," a shortening of Old French escheat, legal term for revision of property to the state when the owner dies without heirs, literally "that which falls to one," past participle of escheoir "befall by chance, happen, devolve," from Vulgar Latin *excadere "to fall away," from Latin ex- "out" (see ex-) + cadere "to fall" (see case (n.1)). Also cf. escheat. The royal officers evidently had a low reputation. Meaning evolved through "confiscate" (mid-15c.) to "deprive unfairly" (1580s). To cheat on (someone) "be sexually unfaithful" first recorded 1934. Related: Cheated; cheating.
cheat (n.): late 14c., "forfeited property," from cheat (v.). Meaning "a deceptive act" is from 1640s; earlier, in thieves' jargon, it meant "a stolen thing" (late 16c.), and earlier still "dice" (1530s). Meaning "a swindler" is from 1660s.
cheater (n.): early 14c., "royal officer in charge of the king's escheats," agent noun from cheat (v.). Meaning "dishonest player" is recorded from 1530s.
cheating (n.): "deceptiveness, swindling," 1530s, verbal noun from cheat (v.).
check (n.1): c.1300, "a call in chess noting one's move has placed his opponent's king (or another major piece) in immediate peril," from Old French eschequier "a check at chess" (also "chess board, chess set"), from eschec "the game of chess; chessboard; check; checkmate," from Vulgar Latin *scaccus, from Arabic shah, from Persian shah "king," the principal piece in a chess game (see shah; also cf. checkmate (n.)). Also c.1300 in a generalized sense, "harmful incident or event."

When the king is in check that player's choices are severely limited. Hence, "sudden stoppage" (early 14c.), and by c.1700 to "a token of ownership used to check against, and prevent, loss or theft" (surviving in hat check) and "a check against forgery or alteration," which gave the modern financial use of "bank check, money draft" (first recorded 1798 and often spelled cheque), probably influenced by exchequeur. Checking account is attested from 1897, American English. Blank check in the figurative sense attested by 1849. Checks and balances is from 1782, perhaps originally suggesting machinery.
check (v.1): late 15c., in chess, "to attack the king; to put (the opponent's king) in check;" earlier (late 14c.), "to stop, arrest; block, barricade;" see check (n.).

A player in chess limits his opponent's ability to move when he places his opponent's king in check. All the other senses seem to have developed from the chess sense: "To arrest, stop;" then "to hold in restraint" (1620s); and finally "to hold up or control" (an assertion, a person, etc.) by comparison with some authority or record, 1690s.

Hence, to check off (1839); to check up (1889); to check in or out (in a hotel, of a library book, etc.). To check out (something) "to look at, investigate" is from 1959. Related: Checked; checking.
check (v.2): "mark like a chessboard, incise with a pattern of squares or checks," late 14c. (implied in checked), from check (n.1). Related: Checking.
check (n.2): "pattern of squares, cross-like pattern," c.1400, short for checker (n.1).
checked (adj.): early 15c., "ornamented with a checkered design," past participle adjective from check (v.2).
checker (n.1): 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" a shortening of Old French eschequier "chessboard; a game of chess," from Medieval Latin scaccarium (see check (n.)).

Meaning "pattern of squares" is late 14c. Meaning "a man or marker 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)).
checker (v.): "to ornament with a checked or chackered design," late 14c. (implied in checkered), from Old French eschequeré and from checker (n.1). Related: Checkering.
checker (n.2): "table covered with a checked cloth," specialized sense of checker (n.1), late 14c. (in Anglo-Latin from c.1300); especially a table for counting money or keeping accounts (revenue reckoned with counters); later extended to "the fiscal department of the English Crown; the Exchequer (mid-14c.; in Anglo-Latin from late 12c.).
checkered (adj.): late 14c., past participle adjective from checker (v.). Checkered past attested by 1831.
checkers (n.): U.S. name for the game known in Britain as draughts, 1712, from plural of checker (n.1). So called for the board on which the game is played.
checklist (n.): also check-list, 1853, American English, from check + list (n.). Two words until c.1880; hyphenated until late 20c.
checkmate (n.): mid-14c., 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."
checkmate (v.): late 14c.; see checkmate (n.). Related: Checkmated; checkmating.
checkout (n.): 1944, from check (v.) + out (adv.). Originally "training given to a pilot for using a specific aircraft;" hotel sense is from 1958.
checkpoint (n.): 1940, from check (v.) + point (n.). Originally an aviator's term for landforms or structures of known height against which the craft's altitude could be visually checked. The "vehicle stop" sense is recorded from 1950.
checkup (n.): also check-up, "careful examination," 1921, American English, from check (v.) + up (adv.), on notion of a checklist of things to be examined. The verbal phrase check up (on) is attested from 1889.
cheddar (n.): type of cheese, 1660s (but the cheese presumably was made long before that), from Cheddar, village in Somerset, England, where it originally was made, from Old English Ceodre (c.880), probably from ceodor "ravine" (there is a gorge nearby).
cheek (n.): Old English ceace, cece "jaw, jawbone," in late Old English also "the fleshy wall of the mouth." Perhaps from the root of Old English ceowan "chew" (see chew (v.)), or from Proto-Germanic *kaukon (cf. Middle Low German kake "jaw, jawbone," Middle Dutch kake "jaw," Dutch kaak), not found outside West Germanic.

Words for "cheek," "jaw," and "chin" tend to run together in IE languages (e.g. PIE *genw-, source of Greek genus "jaw, cheek," geneion "chin," and English chin); Aristotle considered the chin as the front of the "jaws" and the cheeks as the back of them. The other Old English word for "cheek" was ceafl (see jowl).
A thousand men he [Samson] slow eek with his hond,
And had no wepen but an asses cheek.
[Chaucer, "Monk's Tale"]
In reference to the buttocks from c.1600. Sense of "insolence" is from 1840, perhaps from a notion akin to that which led to jaw "insolent speech," mouth off, etc. To turn the other cheek is an allusion to Matt. v:39 and Luke vi:29.
cheeks (n.): "the buttocks," c.1600; see cheek.
cheeky (adj.): 1859, from cheek in its sense of "insolence" + -y (2). Related: Cheekily; cheekiness.
cheep (v.): 1510s, of imitative origin, originally Scottish. Related: Cheeped; cheeping; cheeper. The noun is attested by 1774.
cheer (n.): c.1200, "the face," especially as expressing emotion, from Anglo-French chere "the face," Old French chiere "face, countenance, look, expression," from Late Latin cara "face" (source of Spanish cara), possibly from Greek kara "head," from PIE root *ker- "head" (see horn (n.)). From mid-13c. as "frame of mind, state of feeling, spirit; mood, humor."

By late 14c. the meaning had extended metaphorically to "mood, mental condition," as reflected in the face. This could be in a good or bad sense ("The feend ... beguiled her with treacherye, and brought her into a dreerye cheere," "Merline," c.1500), but a positive sense (probably short for good cheer) has predominated since c.1400. Meaning "shout of encouragement" first recorded 1720, perhaps nautical slang (cf. earlier verbal sense, "to encourage by words or deeds," early 15c.). The antique English greeting what cheer (mid-15c.) was picked up by Algonquian Indians of southern New England from the Puritans and spread in Indian languages as far as Canada.
cheer (v.): late 14c., "to cheer up, humor, console;" c.1400 as "entertain with food or drink," from cheer (n.). Related: Cheered; cheering. Sense of "to encourage by words or deeds" is early 15c. Which had focused to "salute with shouts of applause" by late 18c. Cheer up (intransitive) first attested 1670s.
cheerful (adj.): c.1400, "full of cheer," from cheer (n.) + -ful. Meaning "elevating the spirits" is from mid-15c. Related: Cheerfully; cheerfulness.
cheerio: upbeat parting exclamation, British, 1910, from cheer.
cheerleader (n.): also cheer-leader, 1900, American English, from cheer (n.) + leader. Cheerleading is attested from 1906.
cheerless (adj.): "devoid of comfort," 1570s, from cheer (n.) + -less. Related: Cheerlessly; cheerlessness.
cheers: salute or toast when taking a drink, British, 1919, from plural of cheer (also cf. cheerio). Earlier it is recorded as a shout of support or encouragement (1720).
cheery (adj.): mid-15c., from cheer (n.) + -y (2). The colloquial alternative to cheerful. Related: Cheerily; cheeriness.
cheese (n.1): Old English cyse (West Saxon), cese (Anglian) "cheese," from West Germanic *kasjus (cf. Old Saxon kasi, Old High German chasi, German Käse, Middle Dutch case, Dutch kaas), from Latin caseus "cheese" (source of Italian cacio, Spanish queso, Irish caise, Welsh caws).

Of unknown origin; perhaps from a PIE root *kwat- "to ferment, become sour" (cf. Prakrit chasi "buttermilk;" Old Church Slavonic kvasu "leaven; fermented drink," kyselu "sour," -kyseti "to turn sour;" Czech kysati "to turn sour, rot;" Sanskrit kvathati "boils, seethes;" Gothic hwaþjan "foam"). Also cf. fromage. Old Norse ostr, Danish ost, Swedish ost are related to Latin ius "broth, sauce, juice."

Earliest references would be to compressed curds of milk used as food; pressed or molded cheeses with rinds are 14c. Transferred to other cheese-like substances by 1530s. As a photographer's word to make subjects hold a smile, it is attested from 1930, but in a reminiscence of schoolboy days, which suggests an earlier use. Probably for the forced smile involved in making the -ee- sound. Green cheese is that newly made; the notion that the moon is made of green cheese as a type of a ridiculous assertion is from 1520s. To make cheeses was a schoolgirls' amusement (1835) of wheeling rapidly so one's petticoats blew out in a circle then dropping down so they came to rest inflated and resembling a wheel of cheese; hence, used figuratively for "a deep curtsey."
cheese (n.2): "the proper thing," from Urdu chiz "a thing," from Persian chiz, from Old Persian *ciš-ciy "something," from PIE pronomial stem *kwo- (see who). Picked up by British in India by 1818 and used in the sense of "a big thing" (especially in the phrase the real chiz).

This perhaps is behind the expression big cheese "important person" (1914), but that is American English in origin and likely rather belongs to cheese (n.1). To cut a big cheese as a figurative expression for "look important" is recorded from 1915, and overlarge wheels of cheese, especially from Wisconsin, were commonly displayed 19c. as publicity stunts by retailers, etc.
The cheese will be on exhibition at the National Dairy Show at Chicago next week. President Taft will visit the show the morning of Monday, October thirtieth, and after his address he will be invited to cut the big cheese, which will then be distributed in small lots to visitors at the show. ["The Country Gentleman," Oct. 28, 1911]
cheese (v.): "stop (what one is doing), run off," 1812, thieves' slang, of uncertain origin. Meaning "to smile" is from 1930 (see cheese (n.1)). For meaning "to annoy," see cheesed.
CHEESE IT. Be silent, be quiet, don't do it. Cheese it, the coves are fly; be silent, the people understand our discourse. ["Dictionary of Buckish Slang, University Wit, and Pickpocket Eloquence," London, 1811]
cheese cloth (n.): 1650s, originally cloth in which curds were pressed, from cheese (n.1) + cloth.
cheeseburger (n.): 1938, American English, from cheese (n.1) + ending abstracted from hamburger.
cheesecake (n.): also cheese-cake, mid-15c., from cheese (n.1) + cake (n.). In figurative uses for "soft, effeminate" from 18c. Slang meaning dates from 1934, when a "Time" magazine article defined it as "leg-pictures of sporty females." In its early years this sense of the word often was associated with Marlene Dietrich.
cheesed (adj.): "disgruntled, exasperated," 1941, British slang, origin obscure, connections uncertain. See cheese (n.1), cheese (n.2), cheesy.
cheesy (adj.): "cheese-like," late 14c., from cheese (n.1) + -y (2). Meaning "cheap, inferior" is attested from 1896, perhaps originally U.S. student slang, along with cheese (n.) "an ignorant, stupid person." In late 19c. British slang, cheesy was "fine, showy" (1858), probably from cheese (n.2) and some suggest the modern derogatory use is an "ironic reversal" of this. The word was in common use in medical writing in the late 19c. to describe morbid substances found in tubers, decaying flesh, etc.
cheetah (n.): 1704, from Hindi chita "leopard," from Sanskrit chitraka "hunting leopard, tiger," literally "speckled," from chitra-s "distinctively marked, variegated, many-colored, bright, clear" (from PIE *kit-ro-, from root *(s)kai- "bright, shining;" see shine (v.)) + kayah "body," from PIE *kwei- "to build, make" (see poet).
chef (n.): "head cook," 1830, from French chef, short for chef de cuisine, literally "head of the kitchen," from Old French chief "leader, ruler, head" (see chief (n.)).
Cheka: early Soviet secret police, 1921, from Russian initials of Chrezvychainaya Komissiya "Extraordinary Commission (for Combating Counter-Revolution);" set up 1917, superseded 1922 by G.P.U.
chelate (adj.): "having pincer-like claws," 1826 as a term in zoology; 1920 in chemistry, from Modern Latin chela "claw" (from Greek khele "claw, talon, cloven hoof;" see chelicerae) + -ate (2). Related: Chelated; chelating; chelation.
chelicerae (n.): 1831, plural of Modern Latin chelicera, from Greek khele "claw, talon, cloven hoof," from PIE *ghel-wo-, from root *ghel-una- "jaw," + keras "horn" (see kerato-). Earlier chelicer (1835), from French chélicère.
cheliped (n.): 1859, Modern Latin, from chela "claw," from Greek khele "claw" (see chelicerae) + Latin pod-, stem of pes "foot" (see foot (n.)).
Chelsea: district in southwest London, Chelchuthe (1300), Old English Chelchede (1086), Celchyth (789), Caelichyth (767), probably literally "chalk landing place," from Old English cealc "chalk" (see chalk (n.)) + hyth "landing place." Perhaps chalk or limestone was unloaded here from Chalk near Gravesend in Kent. Chelsea Hospital founded by Charles II, built 1680s, as a home for aged veterans. As a fem. proper name, not in the top 1,000 names in U.S. until 1969, then in the top 100 among girls born 1984 to 1998, peaking at number 15 in 1992.