This report examines employer involvement in youth workforce preparation in the Chicago region. The study sought to develop a better understanding of how employers become involved with youth workforce preparation and how they contribute to the workforce preparation of youth, particularly urban youth facing heightened risk for school failure. It examined the challenges and obstacles to employer involvement, as well as practices and strategies that address challenges associated with employer involvement in youth workforce preparation. Twelve workforce preparation programs were studied, through interviews with employers, employees, and youth program managers and three youth focus groups. The study found that despite different starting points, degrees of involvement, and diverse activities, each of the employers involved in the study provide youth with unique perspectives and experiences that enhance youth development. Further, employers and employees who participated in youth workforce preparation activities benefit through increased job satisfaction, attachment to the workplace, and teamwork skills. Employers also found youth often make positive contributions to the employer's bottom line. Significant challenges encountered when bringing youth and employers together to enhance youth workforce preparation include: 1) developing employer confidence in the integration of youth in the workplace; 2) constrictions in the economy; 3) staff turnover; and 4) clashes of organizational cultures between employers and youth programs. However, these challenges are eased when intermediary organizations are involved in the implementation of employer involvement programs or activities, business objectives are incorporated, and top management is supportive. Recommendations to systemically enhance employer involvement in the Chicago region are also described.