This chapter explores the portrayal of Chicago in the fiction of Saul Bellow, examining the conflict between materialism and visionary idealism that lies at the heart of his work. Starting from the stereotypical characterization of Chicago as the home of brute matter, cynical pragmatism, and the mass production of commodities and physical things, the chapter traces Bellow’s autobiographical search for hidden spiritual truths, connecting this to the Jewish notion of being exiled in a foreign land, vestiges of the soul or the spirit disguised among the quotidian ugliness of industrial America. This conflict between things and ideas, matter and spirit, morality and “the hustle” of economic life, draws on both the conflicts of Bellow’s early life and the wider patterns of Jewish immigration and assimilation. Chicago appears in Bellow’s work as both an overwhelming physical presence and a metaphysical absence, linked to the emptiness of the prairies and haunted by the Jewish-Russian past of Bellow’s family. These contradictions and paradoxes are traced through a close reading of Bellow’s short fiction, as well as his major novels The Adventures of Augie March, Herzog, and Humboldt’s Gift.