Charles Healy dabbled in track and field athletics in his youth, but his talents lay primarily in the pool, where he spent most of his sporting career as a diver, swimmer, and water polo player. It was in the latter sport, as a representative of the Chicago Athletic Association, that he attended the 1904 St. Louis Olympics. His club lost against the New York Athletic Club in its only match, in a tournament that was of questionable Olympic status, but the IOC credits Healy and his teammates with a silver medal.
Healy was more active as a competitive swimmer, however, and focused on this sport primarily after graduating from the De La Salle Institute in 1901. He was still competing through 1913, although he did not attend any more editions of the Olympic Games.