Chamberlain started out in junior hockey with the Ottawa Primrose in 1932-33, One season of senior with Ottawa New Edinburgh and he was off to Northern Ontario. The highlight was playing for the Frood Tigers in 1936-37 when they won the Allan Cup. In 1940-41, Chamberlain signed with the Montreal Canadiens and scored ten goals and 25 points in 45 games. Midway through the following season, he was loaned to the Brooklyn Americans where he finished out the last eleven games of the year.