Background: Social media is an integral part of modern life in which people connect, learn, and share. The content shared on social media can drive behavior change as people, especially adolescents, seek to gain or maintain popularity. #Chronicillness is a rising trend on social media, yet the content and attention it garners remain poorly understood. Objective: This study aimed to analyze Instagram posts related to chronic illness by examining their content and assessing if posts with medical-related content received greater attention. Methods: To study individuals with chronic illness, publicly available Instagram posts were searched for hashtags related to chronic illness. We used a mixed-methods approach which included qualitative analysis of captions, hashtags, and photos for medical conditions, locations, and presence of medical equipment, alongside quantitative analysis to examine the relationship between medical content and attention. Multivariate analyses were performed to determine the odds of medical content Overperforming, a proxy measure for attention. Results: Content analysis of 279 posts revealed caption themes including Medical Experiences, Illness Journey, Connection, and Non-illness Experiences. Among the posts, 97 (35%) included medical content, 52 (19%) featured advertisements, and 10 (4%) depicted invasive medical equipment. Hashtags covered a wide range of 107 different conditions. Posts with medical content exhibited significantly higher odds of overperforming (OR 1.85; 95% CI: 1.01, 3.42), as did posts with photos containing invasive medical equipment (OR 6.19; 95% CI: 1.16, 32.99). Conclusions: Our findings underscore the potential reinforcing effect of sharing medical information on Instagram, the inadvertent promotion of invasive medical procedures as visible signs of illness, and the possibility of adolescents mimicking this attention-generating content. It is crucial to implement strategies for fostering positive and informed interactions within online communities, and to address the potential risks associated with overmedicalization, misinformation, and the commodification of health experiences.