In 1974, Schiller was the Illinois Junior Champion. Schiller played for the University of Chicago team several times at the Pan American Intercollegiate Team Chess Championship. Schiller was the Hawaii action and blitz champion for 1988/89. He was an organizer of the Hawaii International chess festivals 1994–98 including 1998 US Open California Champion 1995. Later that year, he appeared as a chess advisor for the music group Phish on some of the stops for their "Chess Tour" where they played an ongoing game of two chess moves per tour stop and some "band vs. audience" partial games as part of their stage performance. Schiller was an arbiter at several notable games and championships including the FIDE World Chess Championship 2000. While Vladimir Kramnik and Garry Kasparov opted not to participate in the event, they had both endorsed Schiller for this sensitive role during the planning stages.