High Quality Content by WIKIPEDIA articles! "Chicago" is the thirty-eighth episode of the American television series Prison Break and is the sixteenth episode of its second season. It was written by Nick Santora and Matt Olmstead, and directed by Jesse Bochco. The episode first aired on February 5, 2007, making it the first episode to be aired during the February sweeps in the United States. It attained an average of 10.1 million viewers, which is the highest recorded audience for the second season.