This work focused on studying the physicochemical and antioxidant properties changes of varying molecular weight (Mw) chitosan-depolymerization products (CDP)-based films occurring after crosslinking by heat-treatment and Maillard reaction (MR). Based on color properties and browning index, an enhancement of films properties was observed after treatment at 90 °C with a reduction in their water content, solubility and contact angle. Brown MR products were developed in heated films containing glucose thus improving their barrier properties. This effect was more pronounced in lower Mw-CDP based films. In addition, according to TGA, EAB and TS analyses an improvement in heat-treated films thermal stability and mechanical properties was detected and further confirmed through FTIR, X-ray and SEM analyses. The evaluation of the antioxidant potential through four different assays allowed to conclude that glucose addition, thermal treatment and the use of low Mw-CDP highly enhanced the MR-modified films antioxidant capacity. Consequently, MR crosslinked chitosan-based films could be potentially used as an alternative for bioactive and functional packaging effective in food oxidation inhibition, especially using low Mw chitosan derivatives.