Chaikin briefly attended Drake University in Iowa, and then returned to New York to begin a career in theater, studying with various acting coaches, while struggling to survive working a variety of jobs.

"[2] The Open Theatre's most famous and critically acclaimed production, The Serpent, was developed largely from the actors' own experiences, using the Bible as text, but incorporating current events, such as the violence of the 1960s.

In 1970-71 Open Theatre performed Terminal by Susan Yankowitz, touring the production internationally—including at the Shiraz Arts Festival in Iran (1971)--as well as to many maximum and minimum security prisons in the eastern U.S. and Canada.

Chaikin had a close working relationship with Sam Shepard and they co-wrote the plays Tongues and Savage/Love, both of which premiered at San Francisco's Magic Theatre.

Chaikin adapted Texts for Nothing with Steven Kent who directed him in a solo show based on the material which performed at the Public Theater in New York, at the Roundhouse Theatre in London, the American Center in Paris, and in Toronto.

Chaikin directed a number of Beckett's plays, including Endgame at the Manhattan Theatre Club and Happy Days at Cherry Lane Theater.

Chaikin was a lifelong teacher of acting and directing, and lived most of his adult life in New York's West Village, at Westbeth Artists Community.