On December 10, Bondra signed a one-year contract with the Chicago Blackhawks. On December 22, 2006, he scored his 500th NHL career goal at the United Center, in Chicago's 3–1 victory against the Toronto Maple Leafs. Bondra drove to the net and netted the rebound of Jassen Cullimore's shot from the left point past Toronto's Jean-Sébastien Aubin, 6:37 into the third period on the power play. Bondra was the 37th player in league history to reach the 500-goal mark and the fourth player to record his 500th goal in a Blackhawks sweater, joining Bobby Hull, Stan Mikita and Michel Goulet.