Chicago occupies a place in the American imagination as a city of industry and opportunity for those who are willing to hustle. Writers have in no small part contributed to the creation of this mythology; this canon includes Frank Norris, Theodore Dreiser, Upton Sinclair, Carl Sandburg, and Richard Wright. What is it about these authors that make them the classics of Chicago literature? The “essential” books of Chicago enshrine a period during which the city still held a prominent position in the national economy and culture, and embodied for Americans something of their own identity—the value of individualism, and the Protestant work ethic. Notably absent are the narratives from immigrants, particularly those of color: for a city that was a primary destination for the Great Migration of African Americans from the South and the concurrent immigration of Mexicans in the early part of the 20th century, it is remarkable that these stories have not gained significant attention, with the exception of Richard Wright’s. This dissertation interrogates the discourse of ambition and labor in the Chicago literary tradition from the perspective of three Mexican American authors from Chicago—Carlos Cortez, Ana Castillo, and Sandra Cisneros. These authors, faced with late 20th century deindustrialization and the enduring legacy of segregation, engage with the canonical narratives of Chicago by addressing the intersections of race and citizenship as they affect urban space and labor opportunities. Rather than simply offering a critique, however, the Mexican American authors engage in a re-visioning of the city that incorporates the complexities of a fluid, transnational experience, and in doing so suggest the future of urban life in a post-industrial America. / text