Green’s Dictionary of Slang

1. (also chip) to be sexually unfaithful; thus chipping n.

1930		in DARE.
1950		Goldin et al. DAUL 43/2: Chippy around. [...] 2. To be sexually promiscuous. ‘Knock off (stop) chippying around with them blisters (cheap women). We blew (lost) three scores (thefts) account of that.’.
c.1951		N. Algren ‘Watch Out for Daddy’ in Entrapment (2009) 152: I never chippied yet on my Little Daddy.
1956		N. Algren Walk on the Wild Side 176: The next time when you chippy with a date daddy won’t put his mittens on.
1965		L. Bruce How to Talk Dirty 104: Never chippied on your wife one time in eighteen years.
1965		Ward & Kassebaum Women’s Prison 165: [of lesbians] They say when you’re a woman you’re completely loyal and you don’t have to worry about chippying. [...] The women round here chippy maybe three times as much as a man will. Her partner, the aggressor, her dad [...] why he was going home yesterday and she decided she couldn’t wait to chippy, not even two days, so she went to the release cottage and chippied.
1971–2		C. Shafer ‘Catheads [...] and Cho-Cho Sticks’ in Abernethy Bounty of Texas (1990) 200: chipping, n. – two-timing; going out with someone you do not belong to: chipping around on somebody.
1978		H. Selby Jr Requiem for a Dream (1987) 175: She starts chippin with some guy — there aint no cunt in the world that wont chippie onya.
1981		O’Day & Eells High Times Hard Times (1983) 38: He’d been chippying around and had caught a venereal disease, so I gave him the gate.

2. (US) to fool, to deceive.

1958

E. Gilbert Vice Trap 23: Thinking she was chippying on somebody was so funny.

3. (US black) to seduce, to be attracted to.

1967		F. Salas Tattoo the Wicked Cross (1981) 100: She can’t chippy like she used to. Men don’t give her the play anymore. Those that do, get a piece of ass and split on her.
1972		Milner & Milner Black Players 71: The Book says a pimp must never ‘chippy’ (make love to a woman for the pleasure of it).
1989		J. Morton Lowspeak 38: Chippie [...] From the verb to chippy, to have intercourse.

4. to act as a prostitute.

1989

J. Morton Lowspeak 38: Chipping – a version of the corner game. The girl pretends to be a prostitute and then disappears with the cash before any sex can take place.