This study sought to unpack how immigration is associated with youths' educational choices during the transition to college and adulthood. Surveys and school records were collected on 789 youth (ages 1825) with Asian Pacific, Latino, African/Afro-Caribbean, and European backgrounds. The results indicated generational differences in educational choices, such that children of immigrants chose courses of study with higher math and science content than that of their peers with U.S.-born parents. Mediation analyses indicated that children of immigrants reported higher social and economic aspirations than did their peers, and their economic aspirations accounted for part of the generational difference in educational choices. Generational differences in educational choices were also mediated by verbal achievement test scores and perceived English skills.