This chapter is aimed at analyzing the factors that may contribute to improve the Chilean Higher Education System -CHES overall effectiveness. The context of analysis will be the present characteristics of the CHES together with the national policies that condition it, on one hand, and the demands arising from the economic and social sectors, on the other. Several recent landmarks, among them Chile becoming an OECD member, the Higher Education Quality Assurance law implementation, Chilean APEC membership and sustained economic growth have helped to identify a series of challenges that need be faced at country's level in order that the CHES plays the developmental role that it is supposed to play. The Center for Research in Creativity and Higher Education has been involved since 1991 in research and development projects related to Higher Education innovation, quality assurance, and educational research. It is from this perspective that the analysis is made. It is expected that some results of the present analysis may be helpful to other countries whose stages of development share common aspects with the Chilean's. © 2012 Nova Science Publishers, Inc. All rights reserved.