Drafted in the first round as the 24th pick overall in the 1970 NFL Draft, Chester began his NFL career with the Oakland Raiders. Pulling in seven touchdowns and over five hundred yards receiving in his NFL debut season, Chester received the Rookie of the Year award and secured his first of four career Pro Bowl selections. After a trade in 1973 to the Baltimore Colts, Chester played five seasons with them before returning to Oakland. He played with the Raiders in 1980, becoming a Super Bowl Champion after their defeat of the Philadelphia Eagles.