Chitosan, a natural-based polymer obtained by alkaline deacetylation of chitin, is composed of glucosamine and N-acetylglucosamine monomers. Chitosan and its derivatives have a great potential for a wide range of applications in biomedical, pharmaceutical, food, cosmetics, and environmental fields due to its biodegradability, biocompatibility, nontoxicity, and versatile chemical and physical properties. For a breakthrough in utilization, especially in the biomedical field, chemical modification of chitosan will be a key point that can introduce desired properties and enlarge the field of the potential applications of chitosan. Different approaches have been reported to prepare chitosan derivatives and chitosan oligomers with low, medium, and high molecular weights. In this chapter, the properties such as biodegradation, antimicrobial activity, anti-inflammatory and tissue regeneration activity, wound-healing properties, antioxidant activity, and antitumor activity of chitosan and its derivatives are discussed in detail.