The Sinai Urban Health Institute (SUHI) conducts an annual evaluation of our West Suburban Community Health Worker (CHW) Initiative. This document represents the findings of this phased formative and process evaluation. This collaborative approach involved CHWs, supervisors, Health & Medicine conveners, and the SUHI Learning Collaborative facilitators. The evaluation objectives of each project year are intended to build upon the work and findings from the previous year culminating in a mixed-methods approach to documenting the contribution of CHWs to their organizations and to participants’ health and well-being, compiling achievements and lessons learned from the learning collaboratives and identifying best practices for sustainability of CHW programs.