City of Chicago Pipe Band was established in summer 2003 and began performing across the greater Chicago metropolitan area almost immediately. It was created as a competition-focused organisation with ambitions to reach the highest levels of pipe band performance. The band entered its first competitive season in 2004 in Grade 3, was promoted to Grade 2 in 2007, and reached Grade 1 in 2012.

Alongside the main band, the organisation developed a teaching and feeder structure. A training band began in 2008 in Grade 5, later progressing through the grades under the Chicago Scots Pipe Band name. After the flagship Grade 1 band became dormant in early 2013, the wider organisation continued through its development bands and academy programme.

In 2016, the group relaunched as a unified City of Chicago Pipe Band organisation, including competition and development bands plus the Chicago Academy of Piping and Drumming. The band won the 2019 Mid-America Championship and 2019 United States Championship in Grade 3, and made its first trips to the World Pipe Band Championships in Glasgow, placing 8th in Grade 3A in 2019.