Chico served as chief of staff to Mayor Richard. M. Daley from 1992 to 1995, then board president of Daley's Chicago Public Schools from 1995 to 2001. In 2007 he became president of the Chicago Park District. And in 2010 he served seven months as president of the City Colleges board. He ran unsuccessfully for mayor of Chicago in 2011 and is now running for that post again in 2019.