This paper describes the Pathways to Success Project (PSP), which was designed to help students in a low-income community in Chicago more easily navigate the transition from high school to postsecondary education. Statistics from Chicago Public Schools show that only about two-thirds of high school graduates enroll in post-secondary education. This can leave many students ill equipped to succeed in our skills-based economy, and contribute to the ongoing problems of unemployment and poverty. Programs that provide support for students as they work to enroll in a college, university, or career/technical school can be effective at facilitating this transition and helping students gain the skills they need to compete in the 21st century workforce. In addition, collaboration that builds connections between the K-12 system, colleges and universities, and local businesses and organizations, can create a system of support for such programs and further ease for students the process of transition from school to employment. The pilot intervention described here built on existing college and career activities in 3 local high schools and engaged an existing community-based collaborative (the Bronzeville Community Action Council) to help address these issues. During the project, 202 students participated in 10 interactive visits to two local universities and two large, international corporations. Successes and challenges to implementing system-level change with high schools are discussed.