In an increasingly globalized world, mainland China has built an extensive international education industry that prepares students for study abroad, including international schools, third-party college counseling agencies, and visa-application training. Yet, for these international students who shape their academic trajectories around pursuing American higher education, why does returning to China remain a viable and frequently considered option despite contradicting the unidirectional logic that underpins their academic preparation? Exploring this question, the study employs in-depth interviews with five 2000s generation and six post-COVID era international students. Through a comparative analysis of the two cohorts, the study identifies a paradox. Namely, the 2000s generation entered the US with comparatively less privilege and a primarily instrumental set of expectations, yet understood the world as more borderless and fluid when recounting their settlement decision. By contrast, post-COVID students, despite greater privilege and more pluralized expectations of American social and cultural life, perceive settlement as more bounded by rigid geographical and sociopolitical boundaries and more comparative as they seek an affective sense of safety across different cultural environments. Drawing on theories of boundaries, transnational migration, and capital, this research argues that settlement decisions unfold as pathways negotiated through the American Dream, American-recognized and unrecognized privilege, and culture across successive stages of Chinese international students’ migration trajectories. Asking the intimate and personal question “Where is home?” across two generations of Chinese international students therefore interrogates the institutionally assumed linearity from American education to American settlement and challenges the assumption that Chinese international students are a timeless and homogeneous migrant category.