Rolfe was drafted by the senior team in the third round of the 2005 MLS SuperDraft by Chicago Fire, and became a Chicago mainstay, scoring 30 goals in his first four seasons with the club, leading his team in goals with eight in his debut 2005 season, and winning the Lamar Hunt U.S. Open Cup in 2006. Since 2007, Rolfe was one of the Fire's top scorers, scoring 8 goals in the 2007 season and 9 goals in the 2008 season, including a hat-trick and man of the match performance versus the New York Red Bulls.