The life course of Chilean women has experienced profound transformations in the past decades. It has been argued that transitions to marriage and motherhood are being postponed as they are experienced by women at an older age and are becoming events that characterize an increasingly smaller part of the female population. These changes have been often interpreted as part of a process of individualization that would have had reconfigured the cultural norms and social practices regarding gender roles and family formation in Chilean society. Nevertheless, the prevalence and diversification of the practices and norms that shape the transitions to marriage and motherhood at an empirical level remain unexplored. This paper aims to assess the individualization of the life course of women in Chile by empirically analyzing the destandardization of the practices and norms that shape the transitions to marriage and motherhood. By analyzing data from Encuesta Nacional Bicentenario Universidad Católica – Adimark (2009), it demonstrates that changes in the prevalence of the transitions to marriage and motherhood and the diversification of the practices and norms that shape their timing are ambivalent regarding destandardization. These results suggest that the life course of women in Chile is becoming individualized to some extent, but that this trend of cultural and social change is not consistent and uniform, but rather partial and fragmented, nonlinear, and significantly conditioned by the social structure.