Approximately 10-20 million children within the United States lives with a chronic illness. School counselors, by nature of their education and training, are in a prime position to work with and advocate for this population. Students with chronic illnesses struggle with reentry into the school system, as well as a myriad of obstacles related to social, emotional, academic, environmental, or familial factors. School counselors may use their positions within the school system to proactively ensure positive and proactive reentry for students with a chronic illness. The purpose of this chapter is to examine the academic obstacles of children living with a chronic illness. The examination includes discussion of the role of the school counselor to help navigate these obstacles. Finally, the end of the chapter briefly discusses possible areas of growth in knowledge regarding school counselors working with students with chronic illnesses.