Research suggests that bilingual experience is associated with gray matter changes, such that initial language gains are associated with expansion and language expertise is associated with renormalization. Previous studies on language proficiency development primarily focused on between-subjects, quasiexperimental comparisons of monolinguals and bilinguals. This study proposes a new paradigm to examine language expertise and cortical thickness within heritage bilinguals (n = 215), as well as between bilinguals and monolinguals (n = 145), using data combined from eight previous magnetic resonance imaging studies. In general, results highlight variability within bilinguals, finding relationships between cortical thickness and English proficiency that are relatively consistent within monolinguals, but inconsistent within bilinguals. In all participants, higher levels of proficiency in English-monolinguals' only language and bilinguals' second but stronger language-were negatively related to cortical thickness. In bilinguals, higher proficiency in the weaker, albeit first learned, language was positively related to cortical thickness. Moreover, there was an interaction between language group and English proficiency in predicting cortical thickness, such that the relationship between proficiency and thickness was stronger in monolinguals than in bilinguals. Findings also demonstrate that the regions associated with language expertise differ between bilinguals and monolinguals. Future directions for cognitive-developmental neuroscience research in bilinguals are suggested, particularly the longitudinal examination of cortical changes in relation to bilingual experiences.