Osteochondral defects, which involve injury to both the articular cartilage and the underlying subchondral bone, present a considerable therapeutic challenge due to the cartilage’s poor intrinsic ability to regenerate and the intricate, gradient structure of the osteochondral junction. Tissue engineering offers a promising strategy for regenerating this biphasic tissue. Chitosan has attracted significant research interest due to its favorable biocompatibility, controlled degradability, natural antibacterial activity, and structural resemblance to endogenous glycosaminoglycans. Integrating chitosan with 3D printing allows the production of scaffolds with customizable structures, porosity, and mechanical properties suited to patient needs. Moreover, chitosan can easily be blended with various natural polymers to develop composite bioinks that improve osteogenic and chondrogenic potential, thereby enhancing the functional performance of scaffolds. This review examines research literature spanning the period from January 2020 to October 2025. Recent advances include the development of functionalized chitosan derivatives for improved printability and crosslinking, as well as the incorporation of cells and growth factors to create bioactive, cell-laden constructs. This review provides an extensive overview of the physicochemical and biological characteristics of chitosan pertinent to osteochondral regeneration, discusses diverse 3D printing strategies utilized to construct chitosan-based composite scaffolds, and emphasizes their proven potential in improving cellular responses, stimulating bone and cartilage formation, supporting biomineralization, and achieving controlled delivery of bioactive agents. Finally, we discuss the current challenges, such as optimizing scaffold degradation kinetics and vascularization, and future perspectives on the clinical translation of these innovative constructs for effective osteochondral regeneration.