Growing up in Austin, Minnesota, Jon Chaffee started winning championships at a young age by capturing the 1973 Minnesota Golf Association Junior Championship and finishing runner-up in same event in 1974. Chaffee also finished third in the 1974 Minnesota Golf Association Amateur Championship and runner-up in 1975.
Once turned professional, Chaffee began to dominate the local Minnesota golf scene winning the Minnesota Golf Champions event three times 1982, 1983, and 1985, and the Minnesota State Open in 1988. Chaffee also won the Minnesota Section PGA Championship three consecutive times 1989 – 1991 and was named Minnesota Section PGA Player of the Year in 1990 and 1991.
A PGA Member for twenty-five years, Chaffee also spent time on the PGA Tour, playing in more than one hundred tour events and also played in ten PGA of America National Professional Championships.