This report examines the path to college for students in academically advanced programs-- graduates of Chicago's seven Selective Enrollment schools, those who completed International Baccalaureate programs, and graduates who had taken a sequence of at least six honors and two Advanced Placement classes. This report expands on the findings of previous work on the importance of developing specialized supports for the college search and application process for highly qualified students. It focuses on three groups of students: graduates from CPS's selective enrollment high schools, graduates from IB programs, and graduates who have taken a sequence of honors and AP courses in neighborhood high schools. This report presents a portrait of the demographic characteristics and college qualifications of students in these programs. It draws on data from the CPS postsecondary tracking system to examine the college enrollment of these students and compare the kinds of colleges students are qualified to attend to the kinds of colleges to which students apply and to which they ultimately enroll. Finally, it draws on both qualitative and quantitative analysis to identify five areas where academically advanced students in CPS--most of whom are also first-generation college students--face particular challenges as they negotiate the complicated and competitive college application process. This report is not intended to be a rigorous evaluation of the efficacy of selective enrollment schools, IB programs, or AP initiatives. Rather, it is intended to provide critical information that allows school staff and district administrators to assess their own efforts and discuss what it means to develop programs that prepare students to compete for admission to top colleges and universities. The study also shows that AP and IB programs seem to be filling an important gap in neighborhood high schools for students with higher-than-average achievement, and that students graduating from academically advanced programs have ACT scores and grade point averages that are substantially higher than the average CPS student--although there are wide variations among schools. Academically advanced students face distinctive challenges in navigating the road to college--especially if they are first-generation college-goers and cannot count on receiving expert knowledge, the authors conclude. The study included case studies of students, analysis of tests scores, high school transcripts, student surveys and college enrollment data for about 5,600 graduates over two years. Eight appendices are included: (1) Data Used in this Report; (2) Variables Used in this Report; (3) Demographics for Non-IB and Non-AP Students in the Same Schools; (4) Indicators by Programs and Schools; (5) Models Used in this Report; (6) Description of Selectivity Ratings Used in this Report; (7) Adjusting for Missing NSC Data; and (8) College Access versus College Choice. (Contains 16 figures, 7 tables, and 57 endnotes.)