In the City of Chicago, a collaboration between the City Colleges, the Chicago Public Schools, the philanthropic community and the mayor's office has berthed a unique program called the Chicago Roadmap for Success (The Roadmap). The Roadmap aligns resources to ensure that more students have more access to college. One of the keystone features of the Roadmap is the Navigator program. This program is a mentoring program that is designed for high school juniors and seniors as they plan for their postsecondary lives. The Navigator program is run by the City Colleges of Chicago. It has a strong focus on students attending the City Colleges after high school, but Navigators can help students with any postsecondary pathway. This program evaluation study examined the Navigator program from both a quantitative and qualitative viewpoint. Surveys were completed by over 40 students. Interviews were conducted and included both students and Navigator mentors. The results showed a very strong connection between students who had a strong relationship with their Navigator and their matriculation to City Colleges. Additionally, the interviews showed that the mentoring program helped immensely with students understanding how to and wanting to matriculate to college. Interviews also showed an improved perception of both the City Colleges as well as going to college. This dissertation also includes an action plan. The action plan, which is based on the results of the study, calls for an expansion of the mentoring program to not only help mentors be in their schools more often, but also to target Black and Latino male students through specialized Navigator programming. Finally, there is a call to support the Navigators more strongly through better ties to City College resources and an increase in availability to students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]