Chitosan based films endowed with antibacterial features have witnessed remarkable progress as potential wound dressings. The current study aimed at appraising the effects of the molar mass of chitosan (MM) and the film casting acids on the properties of unplasticized chitosan films and plasticized MSO-embedded chitosan films in order to provide best suited film formulation as a potential candidate for wound dressing application. The prepared films were functionally characterized in terms of their qualitative assessment, thickness, density, swelling behavior, water vapor barrier, mechanical and antibacterial properties. Overall, all chitosan films displayed thickness lower than the human dermis even though thicker and denser films were produced with lactic acid. Assessment of the swelling behavior revealed that only high molar mass (HMM) chitosan films may be regarded as absorbent dressings. Moreover, unplasticized HMM lactate (HMM-LA) films furnished lower stiffness and higher percent strain break as compared to acetate films, due to the plasticizing effect of the remaining lactic acid as alluded by the FTIR analysis. Meanwhile, they provided suitable level of moisture and indicated substantial antibacterial activity against S. aureus and E. coli, the most commonly opportunistic bacteria found in infected skin wound. Plasticized chitosan films doped with MSO were significantly thicker and more permeable to water compared to unplasticized films. Furthermore, MSO significantly potentiate the antibacterial effect of chitosan-based films. Therefore, plasticized HMM-LA/MSO chitosan film flashing good swelling behavior, adequate WVTR and WVP, suitable mechanical properties and antibacterial performances substantiated to be a promising antibacterial dressing material for moderately exuding wounds.