Chaykin was born to Jewish parents in Brooklyn, New York. His father, Irving J. Chaykin (1912–2007), was born in Brooklyn, and was a professor of accountancy at City College of New York. His mother, Clarice Chaykin (née Bloomfield, 1921–2012), was born in Winnipeg, Manitoba, but raised in Montreal, Quebec, since the age of three. She graduated from Beth Israel Hospital nursing school in Newark, New Jersey. Chaykin's maternal uncle, George Bloomfield (1930–2011), was a veteran Canadian director, producer, writer and actor who directed Chaykin in a number of projects for film and television.
Raised in New York City, Chaykin studied drama at the University at Buffalo, The State University of New York. He subsequently moved to Toronto, Ontario, where he resided until his death. Chaykin's first marriage, to Canadian producer Ilana Frank, ended in divorce. He was subsequently married to Canadian actress Susannah Hoffmann, with whom he had one daughter, Rose. Best known for having played Jen Pringle in the Anne of Avonlea series, Hoffmann had a supporting role in a 2002 episode of the television series A Nero Wolfe Mystery, in which Chaykin starred.[citation needed]
Chaykin was a dual citizen of the United States and Canada.

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