Chitosan is a natural cationic polymer that dissolves in an acidic environment and forms gels. Its properties depend on the degree of deacetylation and molecular weight. It is a bioactive compound with antibacterial and film-forming properties that allow to increase the regenerative capacity of the skin. Moreover, it is biodegradable, biocompatible, non-toxic, and stable. In this research, chitosan was combined with mandelic and lactobionic acids which are characterized by biological activity and low toxicity. This combination not only has a positive effect on the chitosan solubility, but it also allows to obtain new biomaterials whose positive features of the base ingredients are enhanced by their synergistic effect. The obtained hydrogels were assessed regarding the interaction of chitosan and hydroxy acid molecules, and the stability of the resulting structures was examined. The research was performed by using rheological methods and IR spectroscopy. Chitosan hydrogels made with mandelic acid are characterized by higher viscosity values, as compared to hydrogels containing lactobionic acid. The samples of the obtained hydrogels stored for 7 days showed no signs of degradation and their viscosity values were constantly increasing, which proves the ongoing process of creating new bonds between hydroxy acid molecules and chitosan chains. After this time, the hydrogels with mandelic acid revealed higher viscosity values in comparison to hydrogels made with lactobionic acid. Based on the obtained IR spectra, the shifts of the characteristic chitosan bands as a result of interaction with the tested hydroxy acids were analyzed.