High school sports participation in the United States has increased dramatically over the past 25 years. A corresponding increase in the number of injuries has been noted, particularly in contact sports such as football. This has led medical and sports organizations nationwide to advocate for proper medical supervision of athletes at games and practices.To gather information from Chicago public high schools to gauge how medical supervision for high school sports has changed in 2017 compared with 2003.Cross-sectional study.Survey questionnaires were sent to the athletic directors of all 99 Chicago public high schools to complete via email. The questionnaire survey contained the same questions as in a survey conducted in 2003 by Tonino and Bollier, with the addition of 4 novel questions relating to emergency action plans (EAPs), automated external defibrillators, concussion management policy, and tackling progression drills.The response rate was 66.67% (66/99 schools). Of the 66 responding schools, all with football programs, no school had a physician on the sideline at home games (decrease from 10.6% in 2003), 37.9% had an athletic trainer present (increase from 8.5% in 2003), and 63.6% had a paramedic available (decrease from 89.4% in 2003). In 2017, 65.6% of responding schools had a coach certified in cardiopulmonary resuscitation (CPR) available at practice to handle medical problems, compared with 89.4% in 2003 ( < .001). Regarding the 4 novel questions, 93.9% of the responding schools had proper tackling progression drills in place, followed by 89.1% who had appropriate EAPs and 93.9% with concussion management protocols, including return-to-play and return-to-learn protocols.Although significant improvement was found in athletic trainer coverage, especially at games, physician coverage was lacking and fewer coaches were certified in CPR in 2017 compared with 2003. EAPs and concussion management protocols were present in most Chicago public high schools. Overall, greater medical supervision is needed, which we believe should come in the form of increased athletic training and physician involvement and coverage, given that expert, expedited medical care saves lives.