There are many elements that contribute to, or act as barriers to, a student's academic success. First-generation students face the unequal availability of information and other cultural capital that is crucial to applying to university, as well as the tools needed to successfully navigate undergraduate education. In this work I examine the different elements of cultural capital accumulation that have been shown to impact first-generation college students. I draw on concepts identified in the existing literature including social and cultural capital, institutional assistance, financial situations, and identity conception. I diverge from the existing research to focus on the unique challenges first-generation status itself, and its disconnect from academia, presents students. Drawing on 20 in-depth interviews with first-generation undergraduate students at the University of Chicago, I aim to recognize and document the often-unseen barriers to education, the differences and disparities in attaining academic achievements, and the lived experiences of first-generation students.