This chapter outlines the literary history of Chicago from the city’s inception to the present day. Guided by the idea of Chicago as the crossroads of modern America, the chapter argues that the city occupies a distinctive place in American literature by virtue of its particular geographic and material features. As Chicago developed from prairie outpost to modern metropolis inthe nineteenth century, it became home to a diverse range of literary voices that grappled with representing the city’s new urban realities in its literature. The introduction also outlines how especially women, African Americans, and ethnically diverse immigrants have contributed to Chicago literature, and how successive generations of writers have provided different visions of the city that are influenced by the complex cultural and historical contexts of both the city and America at large. Pointing out that the literary history of Chicago is one of reaction by individual writers to their urban environment, the introduction considers the centrality of Chicago literature for styles and movements such as realism, naturalism, and modernism, before providing a short outline of the book’s five sections.