This dissertation examines the formation of the new middle class in relation to racial divisions in Chicago. I argue that upward mobility in the twentieth century allowed European-Americans to shed racial stigmas and doubts about their abilities to Americanize, creating neighborhoods and ideologies that posited “white” and “middle class” as synonymous. The white middle class embedded segregation in the workplace and in residential areas, while simultaneously solidifying whiteness as an advantageous racial designation. In contrast, black Americans faced widespread economic discrimination and residential segregation, impeding their social mobility and forcing them to seek alternative routes of accomplishment. Class and notions of respectability had deep resonance in the black community as well, creating both conflict against white oppression and intra-race discord. Despite hopes from liberals in the post-World War II era that Northern racial integration would happen along middle-class lines through constructive interactions, the white middle class fled the city. Unlike most studies of urban America, my dissertation does not end with the failure of integration. Rather, it examines how the black middle class continued to work for community stabilization and upward mobility during the civil rights revolution. By exploring this scholarship from both white and black perspectives, I take a more holistic approach to the study of race relations.