This thesis explores how CPS students transition to elite universities like Northwestern University and the University of Chicago, focusing on differences in preparation between selective enrollment and neighborhood schools. The study examines strategies students use to navigate belonging, particularly regarding affluence and exposure differences. It emphasizes the need to avoid generalizations about CPS graduates, highlighting diverse identities and challenges. Qualitative interviews with 12 CPS alumni at UChicago and Northwestern reveal four navigation strategies: community building, identity renegotiation, selecting supportive courses or majors, and symbolic boundary setting. The thesis recommends policies to support CPS graduates’ transition, address preparation gaps, promote equitable opportunities, foster belonging, and reshape the narrative of who belongs in elite academic spaces, prioritizing every student’s value and capability.