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Inequality research has found that a college education can ameliorate intergenerational disparities in economic outcomes. Although much attention has focused on how family resources impact academic achievement, less scrutiny has been given to how social class and related structural contexts impact college attendance. Using the Education Longitudinal Study and multilevel modeling techniques, this study assesses how and to what extent family socioeconomic statuses and school contexts shape college attendance patterns that include attending any college, as well as the likelihood of attending a four-year versus a two-year college. College expectations, academic achievement scores, and extra-curricular participation levels, situated within unique school contexts that are driven by residential and social class segregation, contribute to the cumulative advantages of children from higher SES families. The results from this study also show that these cumulative advantages are positively associated with college attendance and an increased likelihood of attending a four-year versus a two-year school. Nonetheless, these factors cannot fully account for the cumulative advantages that family SES accrues to children during childhood, leading to continued disparities in college attendance patterns, according to family socioeconomic status, that seem to perpetuate economic inequalities.