Itraconazole, a potent antifungal agent, is classified as a Biopharmaceutics Classification System (BCS) Class II drug, exhibiting high permeability but poor aqueous solubility, which significantly limits its bioavailability and therapeutic efficacy. Conventional solubility enhancement techniques such as salt formation, particle size reduction, and encapsulation have shown limited success due to the drug's non-ionizable nature and pH-dependent solubility. Cocrystallization has emerged as a promising pharmaceutical strategy to address these limitations by modifying the crystal lattice structure through non-covalent interactions with pharmaceutically acceptable co-formers. This study explores the formulation of Itraconazole cocrystals with various co-formers to enhance its solubility, dissolution rate, and micromeritic properties, thereby improving its processability in solid dosage forms. The optimized cocrystal formulation (B16) demonstrated a 2.4-fold increase in solubility in 0.1 N HCl (60.47 ± 2.7 µg/mL) and a 25.77-fold increase in phosphate buffer (pH 6.8, 60.57 ± 5.64 µg/mL) compared to pure Itraconazole. The dissolution rate was also significantly improved, with 40.12% drug release in 120 minutes in acidic medium, compared to 32.65% for pure Itraconazole. Furthermore, pharmacokinetic studies in rats revealed a 2.8-fold increase in AUC (3717.58 ng·h/mL) and a Cmax of 206.86 ng/mL, compared to 88.06 ng/mL for the pure drug. The study further examines the industrial feasibility of cocrystallization as an innovative approach for optimizing poorly soluble drugs in commercial formulations. The results highlight the potential of cocrystal technology in overcoming formulation challenges and advancing the development of more effective and patient-friendly antifungal therapies.