This work aimed to modify blue crab chitosan-based films through the Maillard reaction (MR) as a novel alternative to improve their functional and biological properties. To this end, different saccharides (glucose (aldohexose), fructose (ketohexose), xylose (aldopentose) and arabinose (aldopentose)), at different weight ratios 0.5, 1.0 and 2.0% (g/100 g polymer), were studied, and films were heated at 90 °C for 24 h. Based on color changes and browning index measurements, the extent of MR was the highest with aldopentoses, whereas hexoses and particularly ketohexoses, exhibited a relative crosslinking rate. These findings were further reflected with an improvement in treated films mechanical properties and thermal degradation temperatures, and advantageously, barrier properties against UV light and water. In addition, the MR-modified Cs-based films antioxidant activity was interestingly enhanced with mainly aldopentoses. Consequently, MR crosslinked chitosan-based films are promising alternative for active and functional packaging able of food oxidation hindering, especially using aldopentoses.