Chimera played his junior career in the WHL, for Medicine Hat and Brandon. He was selected 121st overall in the 1997 NHL Entry Draft by his hometown team, the Edmonton Oilers, mostly because of his outstanding skating. Chimera played three seasons on the Hamilton Bulldogs, which at that point was the Oilers' farm team in the American Hockey League. In his final season, he was named to the AHL First All-Star team.