Behavioral economics continues to seek evidence-driven research as well as solutions about how individuals can improve their financial decision-making. In the City of Chicago, this approach is a novel method in observing the relationship between residence and postsecondary enrollment rates in the neighborhood, while focusing on the culture and environment of the neighborhood. Prior literature indicates that primarily low-income status, household income, and race identity factor into these results, but no effect alone is strong enough to explain how the culture of a neighborhood can lead to low college enrollment rates. Further research, especially at a local level like South Side Chicago provides a deeper understanding as to how residence in a neighborhood affects a student’s likelihood to enroll in a postsecondary opportunity. Moreover, this can ultimately help improve college enrollment rates in CPS, a challenging issue for all public high schools in the city. Through an analysis of neighborhood characteristics such as walkability, crime rate, household income, and CPS public data about current higher education enrollment rates, this paper explores why three neighborhoods in Chicago—Kenwood, Washington Park, and Woodlawn—have varying college enrollment for students and what the possible underlying explanations are for these low rates in the context of neighborhood social culture and environment. This paper finds that neighborhood residence does relate to how people view and proceed with the possibility of college and that criminal activity may be the priority focus to solve this issue. Following this, the city should be aware that not all neighborhoods are the same; some require different treatment in terms of budgeting, prioritization, and resources for students beyond high school graduation in order for the South Side and CPS overall to achieve a more successful higher education attainment rate for the future generation.