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This mixed- methods study explores how academic match and affordability structure students’ college choices and whether students ultimately enroll and persist in college. We follow the Chicago Public School class of 2018 from the college application process to two years after their expected high school graduation drawing on rich administrative data collected by CPS. We also interview a group of students who are typical of more than a quarter of CPS graduates: those who enroll in an open-access, two-year college, despite having the academic credentials for admission to more selective, four-year institutions. Our research reinforces previous findings in the literature suggesting that college choice continues to matter for getting to and through college, particularly for Black and low-income students.