This dissertation identifies sites of African American aspiration in Chicago during the twentieth century from the Great Depression through the 1950s. African Americans seek to achieve in the context of racial limitation, or as they are referred to in this work, sites of aspiration. Given the persistence of racial inequality in the world, an argument could be made for the perplexing nature of African American aspiration and the futility of such efforts. Yet, research suggests that despite many African Americans' lack of optimism in the country’s ability to transcend racism, many African Americans remain confident in their ability to successfully attain their personal goals, goals that they conceptualize as part of a broader project of advancing the entire race as well. This is because African Americans are the products of a culture that simultaneously places limitations on them based on their race while propagating notions of limitless possibilities and opportunities, an idea popularly known as the American Dream. Put another way, we can understand a site of aspiration as a social sphere when African Americans have sought not only to break down racial barriers to achieve successes previously denied to them on account of their race but to redefine the barometers by which success is measured as well. Furthermore, this dissertation claims that the typical categories scholars use—integrationist or separatist, assimilationist or nationalist—are insufficient to properly and accurately conceptualize the African American experience in the United States. African Americans more than any other group in the United States understand both the power of the nation’s founding ideals and creed, and the burden of a history that contradicts those ideas. This dissertation offers another reading of the African American experience, one where instead of a wholesale rejection or acceptance of the American Dream, African Americans negotiate the liminal space between restriction and possibility. To answer this question this dissertation explores five sites of aspiration in Chicago during the middle of the twentieth century. The first chapter focuses on the efforts made to save the Supreme Liberty Life Insurance Company during the Great Depression. Chapter two focuses on the history of the south side’s Parkway Community House, specifically the role it played in helping African Americans successfully meet the challenges of life on the home front during World War II. Chapter three turns to how African Americans sought to access housing in the aftermath of World War II. Chapter four focuses on John H. Johnson, owner of the Johnson Publishing Company and Ebony magazine, and his efforts to convince advertisers that the African American market was a viable one and to instill and consumer citizen ethos into his African American readers. The fifth and final chapter will focus on the Nation of Islam and its alternative vision to the consumerism personified in American culture and propagated to and by many African Americans during the 1950s.