Chile has experienced considerable educational expansion over the past few decades, as well as a privatization reform in 1981 that introduced full parental choice through a voucher system, in the context of a market-oriented transformation of the country. Using a cohort analysis of the 2001 Chilean Mobility Survey, this article examines trends in educational stratification in Chile over the past 50 years, with a focus on the changes that followed the privatization reform. The analysis shows that, in line with international findings, there is “persistent inequality” of educational opportunity across cohorts in Chile. Persistent inequality is not total, however. There is a small but significant increase in inequality in the transition to secondary education, which is cotemporaneous with the market-oriented transformation. Furthermore, when school sector-a form of “qualitative inequality” expressed in the distinction among public, private-voucher, and private-paid schools-is considered, the analysis suggests an increase in the advantages that are associated with private-voucher schools after the privatization reform, as well as in the benefits of attending private-paid schools during and after the reform. The article concludes by discussing the relationship among economic context, privatization reform, and educational inequality.