In recent years scholars representing various academic disciplines have carried on government sponsored research to determine the impact of integration on black and white students. These scholars have produced such nationally influential and widely adopted studies as the first “Coleman Report.” Nevertheless, the research has made little reference to the history of integration and has therefore called into question whether such practices are best for every school system. Moreover, the studies have had broad foci, rarely concentrating on specific school grades or areas of student growth and development. Using the secondary schools of Chicago, both high schools and junior high schools, this essay will examine the historical integration-segregation dilemma from the passage of the first Illinois school law in 1825 to the solidification of the segregation era in the 1930s. It will also provide information on the structural impediments to black students' academic advancement as well as identify the forces which sought to establish a vocational caste system to limit the employment opportunities for these students.