Chakiris was born in Norwood, Ohio to immigrants from Greece. He made his film debut in 1947 and for several years he appeared in small roles, usually as a dancer or a member of the chorus in various musical films. He was one of the dancers in Marilyn Monroe's "Diamonds Are a Girl's Best Friend" number in Gentlemen Prefer Blondes (1953) and also appeared as a dancer alongside Rosemary Clooney in White Christmas.

His biggest success came with the film West Side Story (1961), for which he won the Academy Award for Best Supporting Actor for his role as Bernardo.

Chakiris has also appeared on Broadway and television, and in the early 1960s embarked on a career as a pop singer which resulted in a couple of minor hit songs.

Chakiris last acted in a 1997 episode of the sitcom Last of the Summer Wine and has given occasional television interviews since then. These days he is mostly retired, and has taken up jewellery making as an occupation.