As the number of people living with chronic illness in the United States rises, it is imperative that medical school prepare physicians who are capable of caring for these patients. This article outlines a creative educational intervention to teach third- and fourth-year medical students about caring for chronically ill people. All students at Weill Medical College, Cornell University, make home visits to homebound older adults with an interdisciplinary team as part of a mandatory Primary Care Clerkship. Under their guidance, students observe the myriad challenges facing homebound older adults. Afterward, students create a project, using original or found art, to express their reactions and thoughts. Students present projects to peers in a small group, with multidisciplinary faculty mentors framing the discussion. To evaluate the intervention, students responded to a nine-item questionnaire and a series of open-ended questions. Quantitative and qualitative analyses show consistently strong positive responses to the experience. Most students (95.0%) felt that they learned about the complexities of chronic illness care from their home visits. The opportunity to express reactions through a creative project received positive responses with 97.0% of students responding favorably. Ninety-seven percent felt that the discussions with colleagues and faculty increased knowledge of chronic illness care. Nearly all (97.0%) felt they had a better understanding of team and that attitudes toward the chronically ill were positively affected. The coupling of the creative arts with home visits is an effective tool for teaching about chronic illness and may be a useful model for medical schools interested in expanding their chronic illness curriculum.