Chipchura began his major junior career with the Prince Albert Raiders of the Western Hockey League in 2002–03. Following his second season with the Raiders, he was drafted by the Montreal Canadiens. On March 25, 2006, Chipchura was signed to a three-year entry-level contract by the Canadiens and joined AHL affiliate the Hamilton Bulldogs to complete the 2005–06 season. In 2006–07, Chipchura remained with the Bulldogs. After posting 39 points in the regular season, Chipchura added a further 6 goals and 13 points in the playoffs to help Hamilton capture the Calder Cup. In the 2007–08 season, Kyle played his first NHL game on October 10, 2007. He netted his first goal later that month on October 20 against the Buffalo Sabres. On December 2, 2009, he was traded to the Anaheim Ducks for a fourth-round pick in 2011. Chipchura found a checking-line role within the Ducks and posted 6 goals and 6 games to finish out the 2009–10 season. His second season with the Ducks proved less successful, in struggling for a regular roster spot, Chipchura finished with just 2 assists in 40 games. Released by the Ducks to explore free agency, Chipchura signed to a one-year contract with the Phoenix Coyotes on July 19, 2011. After five seasons within the Coyotes organization, Chipchura left the NHL as a free agent and signed his first contract abroad, agreeing to a one-year deal with Slovakian outfit HC Slovan Bratislava of the KHL on July 17, 2016. Chipchura in his lone season with Bratislava in 2016–17, appeared in 59 games and posted 13 goals and 29 points. fighting Shane O'Brien in 2009 On June 2, 2017, Chipchura continued in the KHL, however moved to Chinese outfit, HC Kunlun Red Star on a one-year deal. At the conclusion of the 2017–18 season, having seen his production drop to just 11 points in 56 games, Chipchura opted to return to Slovan Bratislava as a free agent, agreeing to a one-year deal on July 17, 2018.
International play
Chipchura attended Team Canada's selection camp prior to the 2005 World Junior Championships and was expected to make the team despite being only 18. During practice with the Raiders, however, he suffered a severed Achilles tendon and was not able to be selected as a member of the gold-medal-winning Canadian team. The following year, Chipchura was invited to try out again for the 2006 World Junior Championships. After being selected for the Canadian team, Chipchura was named team captain by head coachBrent Sutter on December 16, 2005. This made Chipchura the second Montreal Canadian to ever wear the 'C' for Canada.
