In the present study, the phytochemical content and the antioxidant activity in the inflorescences of the monoecious hemp cultivar Codimono grown in southern Italy were assessed, and their elicitation was induced by foliar spray application of 50 mg/L and 250 mg/L of chitosan (CHT) at three different molecular weights (low, CHT L; medium, CHT M; high CHT H). The analysis of the phytochemical profile confirmed that cannabinoids were the most abundant class (54.2%), followed by flavonoids (40.3%), tocopherols (2.2%), phenolic acids (1.9%), and carotenoids (1.4%). Cannabinoids were represented almost exclusively by cannabidiol, whereas cannabigerol and Δ9-tetrahydrocannabinol were detected at very low levels (the latter was below the legal limit of 0.3%). The most abundant flavonoids were orientin and vitexin, whereas tocopherols were mainly represented by α-tocopherol. The antioxidant activity was found to be positively correlated with flavonoids and tocopherols. Statistical analysis revealed that the CHT treatments significantly affected the phytochemical content and the antioxidant activity of hemp inflorescences. Notably, a significant increase in the total phenolic content (from +36% to +69%), the α-tocopherol (from +45% to +75%) and β+γ-tocopherol (from +35% to +82%) contents, and the ABTS radical scavenging activity (from +12% to +28%) was induced by all the CHT treatments. In addition, treatments with CHT 50 solutions induced an increase in the total flavonoid content (from +12% to +27%), as well as in the vitexin (from +17% to +20%) and orientin (from +20% to +30%) contents. Treatment with CHT 50 L almost always resulted in the greatest increases. Overall, our findings indicated that CHT could be used as a low-cost and environmentally safe elicitor to improve the health benefits and the economic value of hemp inflorescences, thus promoting their employment in the food, pharmaceutical, nutraceutical, and cosmetic supply chains.