Digital transformation of the healthcare industry is being accelerated due to the evolution of digital intelligence information technology such as artificial intelligence (AI), Internet of Things (IoT), and big data. As online-to-offline (O2O)-based consumption life, based on platforms, becomes routinized along with the COVID-19 pandemic, the O2O platforms on medical activities are gaining attention. This study targeted the medical information O2O platform users and aimed to verify the effects of service quality factors on the platform users’ continuous use intention with the mediation of perceived usefulness and perceived convenience. Based on previous studies, four such factors: context-based affordability, immediacy of connection, reliability, and safety were defined as the medical information O2O platform service quality components. This study targeted 369 users of medical information O2O platforms with market dominance in Korea and conducted a questionnaire survey. According to analysis results, context-based affordability and immediacy of connection had a positive (+) effect on perceived usefulness and convenience, and they were confirmed to affect continuous-use intention with the mediation of the perceived usefulness and convenience. Meanwhile, reliability did not affect the perceived usefulness and convenience, whereas safety had a positive (+) effect on perceived usefulness but did not have the same effect (+) on perceived convenience. Consequently, it was ascertained that context-based affordability and immediacy of connection are more important factors to the medical information O2O platform consumers than reliability and safety.