Since 2004, the Consortium on Chicago School Research (CCSR) has tracked the postsecondary experiences of successive cohorts of graduating Chicago Public Schools (CPS) students and examined the relationship among high school preparation, support, college choice, and postsecondary outcomes. The goal of this research is to help CPS understand the determinants of students' postsecondary success and to identify key levers for improvement. This document summarizes and presents the key findings of the second report of a series which looks beyond qualifications to examine whether CPS students who aspire to four-year colleges are effectively participating in the college search and application process and where they encounter potholes on the road to college. Drawing on prior research, this report examines both how students manage the college application process and what types of colleges students apply to and ultimately enroll in. (Contains 2 figures and 3 endnotes.) [For the first report in this series, "From High School to the Future: A First Look at Chicago Public School Graduates' College Enrollment, College Preparation, and Graduation from Four-Year Colleges," see ED500519. For Case Studies, see ED500518. Karen Roddie, Jamiliyah Gilliam, and Desmond Patton also contributed to this report.]