Early in the 20th century, high rates of international migration from Europe and an increasing number of migrants from the South were rapidly changing the composition of cities in the northern United States. Within this dynamic environment, families faced a more complex set of decisions for the preferred economic roles of their members. For adolescents, families chose between the immediate economic rewards of sending them into the workforce and deferring benefits by extending their educational careers. This article uses the 1920 Public Use Microdata Sample to examine racial and ethnic variation in school enrollment for adolescents aged 14 to 18. It proposes a conceptual model that uses a variety of social, economic, and cultural forces to anticipate differences in schooling between international immigrants and domestic migrants, as well as across generations of both groups. The statistical analyses reveal large racial and ethnic differences in schooling for both boys and girls. The most surprising finding is for second-generation black female migrants from the South, who were significantly more likely than were all other groups of female adolescents to be enrolled in school. The authors speculate that this result is due to a combination of "immigrant optimism" and restricted employment opportunities for second-generation black female migrants in the North.