As of the 2014 season, the league consists of three separate travel teams. The Syndicate is the Outfit's A-team, representing the league in bouts counting toward WFTDA rankings. The Outfit added the Shade Brigade, the B-level team, in January 2009. The Shade Brigade usually competes against lower-ranked WFTDA leagues or the B-teams of leagues that have higher rankings. Due to the large number of new skaters joining the Outfit at the end of 2010, the league voted to start an additional C-level team called the Shakedown for newer skaters. The Shakedown began competing in August 2011. All Chicago Outfit home games are held in the Windy City Fieldhouse.
The Outfit is a democratic league, run by the skaters and for the skaters. The league has a long history of contributing charitably to several other non-profit organizations, including the Howard Brown Health Center, Ignite the Spirit, Family of Moxie Mayhem, Derby News Network, Help Tequila, Girls Rock! Chicago, the American Cancer Society, and Rape, Abuse, and Incest National Network (RAINN). The Outfit also coaches the Chicago Riots, which is a junior roller derby league consisting of girls ages 12 to 17.