Several barriers face students as they attempt to bridge the gap between their educational aspirations and college degree attainment: poor academic preparation that undermines minority and low-income students’ access to and performance in college, students’ difficulties in navigating the college enrollment process, and the declining real value of financial aid combined with rising college costs. This paper draws on the findings from a multi-year research project at the Consortium on Chicago School Research, or CCSR, at the University of Chicago that is studying the college qualifications, enrollment, and graduation patterns of Chicago graduates and examining the relationships among high school preparation, support, college choice, and postsecondary outcomes.