He was not drafted by a team but the Blackhawks signed Bollig to a two-year entry-level contract and put him on their AHL farm team, the Rockford IceHogs. He played 2 seasons with the IceHogs and was called up to the Blackhawks on February 28, 2012. He scored his first NHL goal on April 14, 2012, against Mike Smith of the Phoenix Coyotes in a playoff game. Bollig also portrayed Will Cross, age 12 in the 2002 film Defiance. On June 24, 2013, He won the Stanley Cup with the Blackhawks after they defeated the Boston Bruins 4 games to 2 in the 2013 Stanley Cup Finals.