Chaykin was born 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.