For over a century, Chicago has played soccer. This work explains the early history of the game in the Second City, beginning with the 1887 formation of the Chicago Football Association, and concluding with the 1939 season and Chicago Sparta’s National Open Cup win, which brought the trophy to the city for the first time. This study chronicles the early British immigrants who first transported and organized the game in Chicago. It documents the myriad ethnic groups and native born players that kicked in the city’s many leagues, and examines the many championship tournaments, teams, and players that made Chicago one of the nation’s early soccer powers.