Academic match is a well-documented phenomenon shown to be closely tied to postsecondary outcomes such as college graduation rates and earned income. This study explores the association between college net cost and academic match using student-level data of Chicago Public Schools seniors from the 2020-2021 school year. I find significant evidence of unique financial pressures placed on academically competitive, low-income students who are likely to receive relatively poor financial aid packages that could disincentivize them from attending a match college. This represents a new factor for consideration in studying patterns of academic match, and I argue how certain strategies in postsecondary advising and targeted funding could improve graduation rates among low-income competitive students.