Over the last years, chitosan has demonstrated unparalleled characteristics for regenerative medicine applications. Beside excellent antimicrobial and wound healing properties, this polysaccharide biopolymer offers favorable characteristics such as biocompatibility, biodegradability, and film and fiber-forming capabilities. Having plentiful active amine groups, chitosan can be also readily modified to provide auxiliary features for growing demands in regenerative medicine, which is constantly confronted with new problems, necessitating the creation of biocompatible, immunogenic and biodegradable film/scaffold composites. A new look at the chitosan composites structure/activity/application tradeoff is the primary focus of the current review, which can help researchers to detect the bottlenecks and overcome the shortcomings that arose from this intersection. In the current review, the most recent advances in chitosan films and scaffolds in terms of preparation techniques and modifying methods for improving their functional properties, in three major biomedical fields i.e., tissue engineering, wound healing, and drug delivery are surveyed and discussed.