The Windy City entered AAABA action in 1987 at the Livonia Regional. The franchise made its Johnstown debut the following year represented by Team Chicago Northwest. After that winless campaign, Adam Warnbach's Northwest team surged to a 4-win tournament in the expanded 1989 season, picking up their first win 5-3 over Cleveland in Windber. The club also won against New York City, Zanesville, and Altoona, losing both games to Baltimore. They returned with a 3-win 1990 tournament. Team Chicago Northwest competed in 5 tournaments, winning 7 games.
In 1996, the Glen Ellyn Jam led by Keith Romer picked up the Chicago banner and earned at least 1 win in all 8 tournaments between 1996 and 2008. The Jam were unable to win any of the 4 regionals, but were a surprising runner-up in 2006. After losing a rescheduled opening night contest to Johnstown by 10 runs, the Jam responded with a double-header victory on Wednesday against Chicago-South Shore (16-2) and Buffalo (10-2). They then eliminated Cleveland (8-1) and Maryland State (5-4) before earning a major victory over the 3-time defending champions from Baltimore (5-1). The Jam had to face the Orioles once again in the championship, but came up on the short end of a close 5-3 game.
The Glen Ellyn Jam disbanded in 2009 and the franchise was left without a representative for the season, but the following year saw the introduction of the Des Plaines Patriots. The team made a strong first impression with a 3-2 showing in Johnstown. The Patriots quickly exited the upper bracket in 2011 at 0-2, but the future looks bright for the Chicago-Metropolitan franchise. The club has the 7th best winning percentage of the 19 active franchises.