Over the past three decades, privatisation and school choice have been introduced and embodied in the vocabulary of several national education policies. This study aiming to examine the phenomenon of private schooling and the factors that affect parental school choice outlined a comprehensive framework of the national policies about private schools and school choice in Greece and Sweden. The case study design of the research provided an in-depth exploration of the two national contexts, enriching the study with empirical data. Twenty semi-structured interviews with education professionals and parents from both countries shed light on the reasons behind the school choice towards private schools. Regarding the findings of the research, several kinds of educational inequalities and social segregation were identified because of the fact that not all parents have access to school choice under equal terms.