Natural fruit vinegars, derived from various fruits, enhance culinary experience and offer potential health benefits due to their bioactive compounds. In this study, fruit vinegars (apple, blackcurrant, and cherry) were used as natural solvents for producing chitosan films, introducing an environmentally friendly approach. Fruit vinegars and chitosan-based solutions were examined for their antioxidant and antimicrobial properties. In turn, the obtained chitosan films were characterized by their antimicrobial, mechanical, and structural properties. Both fruit vinegars and film-forming chitosan solutions showed antioxidant activity, and chitosan–cherry vinegar solutions exhibited the highest antiradical and ferrous ion-chelating effect. All solvents and chitosan-based solutions were characterized by antimicrobial properties, especially against Pseudomonas aeruginosa (inhibition zone > 28 mm). Antimicrobial activity was also preserved in the case of chitosan-based film, especially when produced with cherry vinegar, which showed activity against the broadest spectrum of bacteria. The largest zone of inhibition for all samples was observed for P. aeruginosa in the range of 19 mm from the inhibition zone to >28 mm, depending on the type of vinegar used as a solvent. The conducted tests showed that the type of vinegar used also affects the mechanical parameters of the films obtained, such as elongation at break, for which values were recorded from 3.97 to 4.93 MPa, or tensile strength, for which the values were recorded from 48.48 to 70.58 MPa. The results obtained demonstrate that natural fruit vinegars, serving as chitosan solvents, can be an alternative to traditionally used acidic solvents, yielding films with favorable properties.