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.

 

Chimera played two seasons for Edmonton before being traded to the Phoenix Coyotes for draft choices. Because of the NHL lockout, he did not play the following season and went to Italy in the A.S. Mastini Varese Hockey. Chimera was subsequently dealt to the Columbus Blue Jackets, without playing a game in Phoenix, as part of a trade for Geoff Sanderson. He presently plays on the Blue Jackets' 3rd line.

 

He was a member of the 2007 Canadian IIHF World Championship team that won gold in a 4-2 win against Finland in Moscow.