Chipchura was born in Westlock, Alberta. He played minor league hockey in nearby Legal and Westlock, and attended high school at R. F. Staples Secondary School and Carlton Comprehensive High School during his major junior career with the Prince Albert Raiders.\n', '

Chipchura began his major junior career with the Prince Albert Raiders of the Western Hockey League (WHL) 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.\n', '

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.\n', '

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