Jeff Chychrun was selected in the second round, 34th overall, by the Philadelphia Flyers in 1984 NHL Entry Draft. Chychrun played three years of junior hockey in the OHL with the Kingston Canadians. During his last season with Kingston, the 19-year-old scored four times and collected 25 points. When the Flyers drafted him in 1984, they were impressed by his size and agility and a willingness to play the role of policeman if necessary.
Chychrun played his first NHL game in 1986-87 after spending 74 games in Hershey with the AHL's Bears. His first full season came two years later, when he suited up for all 80 Flyers games, scoring a goal and five points while spending 245 minutes in the penalty box. Chychrun's aggressive style was to the Flyers' liking, and he reminded fans of the good old days when the team was known as the Broad Street Bullies. Chychrun missed just one game the next year, but his penalty total rose to 248 minutes, while scoring nine points, which was his career best.
After starting the 1991-92 season with the Los Angeles Kings, Chychrun was traded to the Pittsburgh Penguins where he played 17 games during their Stanley Cup winning season. In 1992-93, he retired to the L.A. Kings for another 17 games but was unable to land a regular spot in the lineup. Chychrun attempted to catch on with the Edmonton Oilers in 1993-94 but was cut loose after playing just two games. Chychrun played 262 regular-season NHL games, scoring two goals and 25 points with 744 minutes in penalties.