Chitosan has wide applications in the field of medical dressings due to its good biomedical properties. This review provides the application status and technical analysis of chitosan medical dressings. First, we introduce the source and chemical structure of chitosan. Then, we investigate the mechanism of chitosan showing different medical properties. We also show the application of supramolecular chitosan-based hydrogels in the dressing field and the formulation optimization and the preparation technology of chitosan dressings for fabricating chitosan-based dressings with various morphologies and medical functions. After that, we introduce the research process of the modification method of chitosan dressings including single modification, blending modification, crosslinking modification, etc. Finally, based on the study of the medical effects of chitosan dressings, we analyze the existing problems in the preparation process and propose corresponding solutions from the aspects of the morphology, clinical feedback effect, and future development trends. This paper can provide a reference for further studies of skin tissue engineering and the development of new chitosan medical dressings.