Sara Paretsky’s contemporary hard-boiled detective novels featuring female private investigator V. I. Warshawski have placed Chicago firmly on the crime fiction map. In a series of twenty detective novels, Paretsky has depicted the uncompromising and passionate Warshawski as she navigates multicultural, industrial Chicago, taking on capitalism, patriarchy, and blue- and white-collar crime. This chapter examines Paretsky’s use of the crime genre’s conventions to investigate and represent crime in Chicago, arguing that gender, race, and class are central to this creative and imaginative process. The crime genre focuses on the quest for truth and justice for victims, themes which are central to Paretsky’s feminist sensibility and social criticism. The analysis centres on Paretsky’s triangulation of feminism, blue- and white-collar crime, and politics in her representation of Chicago. Stylistically hard-boiled but with explicit demonstrations of anger, empathy, and emotional intelligence, Paretsky’s Warshawski embodies a feminist challenge to the traditional masculinist tough guy detective character in her ongoing creative exploration of the history and geography of Chicago crime.