We examine how race, sex and poverty contribute to the likelihood of attending two- and four-year colleges in Chicago and Toronto. In each city, we use longitudinal data on high school students and their postsecondary trajectories in order to explore how race and sex may impact differentially upon their educational pathways. Our analyses are informed by an intersectionality perspective, wherein we understand that life chances are shaped by the various traits and identities that individuals possess. In Toronto, Black males are less likely than all other groups to attend four-year colleges. We also find that two-year colleges appear to fulfill a different role in Toronto than they do in Chicago; that is, serving populations who may have been tracked into non-academic course selections in high school. We contextualize our findings within the very different political, cultural, and historical contexts of Ontario and Illinois.