At Lawrence High, Chiles was All-Nassau County and New York Times All-Stars first team. Chiles transferred to WVU from Wesley Junior College in Dover, Delaware. He won junior college All-American honors there as a running back in 1970. In the Sterling Silver Bowl, he carried the ball 33 times for 204 yards and one touchdown. He was named Wesley's Back of the Year and Athlete of the Year.

Chiles was considered to built along the lines of Garrett Ford and Eddie Williams and came to WVU with very high credentials. He was known as "Honey Chiles" by his teammates. As a junior he started slow but came on strong to be the team's third leading ball carrier with 97 rushes for 486 yards and six touchdowns. He was named to the ECAC All-Star team for the week of November 13 for his showing against Virginia Military Institute (23 carries, 152 yards, 1 TD). Chiles gained 888 yards in his career at WVU and is listed as the 16th all-time yardage leader for fullbacks.