Chipchura was drafted with the 18th overall pick by the Montreal Canadiens in the 2004 NHL Entry Draft. He made his NHL debut with the Canadiens on October 10, 2007 in a 3–2 win against the Pittsburgh Penguins. He scored his first NHL goal in a 4-2 win against the Buffalo Sabres on October 20, 2007. On December 2, 2009, the Canadiens traded Chipchura to the Anaheim Ducks for a fourth-round pick in the 2011 NHL Entry Draft. He played 2 seasons with the Ducks before he was released by the Ducks. On July 19, 2011, he signed a one-year contract with the Phoenix Coyotes.