Feed additives and fat sources have been used to meet high productive dairy cow energy requirements. This study aimed to evaluate dietary chitosan and soybean oil effects on mid-lactation dairy cow intake, digestibility, metabolism and productive performance. Twenty-four Holstein cows (134.7 +/- 53.1 days in milk, 36.14 +/- 5.32 kg/day of milk yield, and 581.2 +/- 73.6 kg of body weight, Mean +/- SD) were used in a replicated 4 x 4 Latin square design with 21-d periods, with 14 d of adaptation and 7 d for data collection. The treatment arrangement was a 2 x 2 factorial design with two levels of chitosan (0 and 4 g/kg of dietary dry matter - DM) and two levels of soybean oil (0 and 33 g/kg of dietary DM). Chitosan decreased intake only in diets without oil (P < 0.05). Regardless of fat addition, chitosan increased DM and CP digestibility (P < 0.05). Soybean oil and chitosan increased total serum cholesterol (P < 0.05). Chitosan diet had higher urea plasma concentration than control diet (CON) (P < 0.05). Over all, soybean oil increased propionate and decreased acetate ruminal molar proportion, and therefore decreased acetate:propionate ratio (P < 0.05). Chitosan decreased milk yield, nitrogen use and feed conversion efficiencies in oil-diets (P < 0.05). Soybean oil decreased short and medium milk fatty acids concentration (P < 0.05). Chitosan had no effect on long-chain milk fatty acids in diets with soybean oil (P > 0.05). However, in free oil-diets, chitosan increased milk polyunsaturated fatty adds concentration, nitrogen and energy efficiency. Chitosan addition in free-fat diets improved feed efficiency, increased milk unsaturated fatty acids concentration and association with soybean oil negatively affect animal performance.