Idlers, Outliers and Dependents: The Free Labor Order in Industrial Chicago, 1870-1930 examines the rise and fall of what I term “the free labor order,” a parallel social order that patterned individual duties and obligations around wage work. Chicago’s new Municipal Court, opened in 1906, picked up—in part—where nineteenth century Police Courts left off. Enforcing the terms and tenets of the free labor order through specialized Morals, Domestic Relations, Vagrancy and Criminal branches, the Court evidenced the important association between steady wage work and social, legal and citizenship status. This association was further bolstered by a string of municipal investigations into vice, crime and race. The outliers of the free labor order are the active agents in this study, which explores the ways vagabonds, sex workers and Black migrants received—but also reshaped—the terms of the free labor order by contesting its social, legal and economic constructions of dependency, its labor hierarchies and its circumscription of their basic social and economic rights. By placing vagabonds, sex workers and migrants at the center of urban life, my study highlights the stories and struggles of a resilient but forgotten workforce and explores the racial and gendered characteristics of wage work, while examining the ways outliers formed their own relationships to the economy. The study concludes by positioning the trials and experiences of the Progressive Era outlier as a critical, though neglected, narrative in the nation’s response to economic collapse in the 1930s.