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In 2005, the University of Chicago Pritzker School of Medicine unveiled an institution-wide Roadmap to Professionalism designed to both increase awareness about issues of medical professionalism across the institution and gain a better understanding of how medical trainees' professional behaviors' change during their training as a result of the medical learning environment. The authors describe the institution's approach and progress to date. To gain buy-in from all levels of learners at the Pritzker School of Medicine, the initiative uses vertically integrated advisory groups to engage medical trainees in the assessment and development of experiential workshops and evaluation initiatives based on the principles outlined in the American Board of Internal Medicine / American College of Physicians / European Federation of Internal Medicine's Physician Charter for Medical Professionalism. Advisory groups provide targeted assessments and programming at each stage of the medical learner: preclinical students, clinical students, residents, and faculty. Surveys of medical students' perceptions of professionalism have provided an important baseline assessment of the learning environment, from which the professionalism steering committee plans to target future curricular interventions. Efforts to engage residents have focused on experiential workshops addressing interactions with the pharmaceutical industry and patient-care hand-offs, as well as the development of a tool for patients to evaluate their resident physicians. The establishment of a series of medical education grants aimed at supporting professionalism research has helped raise faculty awareness. This institution's approach and experience to date may provide valuable lessons for educators and leaders aiming to assess and improve their learning environments.