In Chicago, selective enrollment schools are elementary, middle, or high schools to which students must apply. Students are then assessed based on their grades, test scores, and sometimes attendance. This study focuses specifically on student and parent experience before, during, and after their selective enrollment high school experience through qualitative analysis of interviews. All students in this study had a positive experience academically and had satisfaction with their high school experience due to the opportunities that it gave them and regardless of race or class, students felt a sense of belonging within their selective enrollment high school community. But low-income students of color faced more barriers to selective enrollment during their application process and faced more challenges during their experience attending a selective enrollment high school. Additionally, only low-income students noted that they felt lucky to have attended a selective enrollment high school rather than feeling entitled or deserving of their selective enrollment experience.