In the literature, solubility values of itraconazole complexed with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) were found which were still much too low to obtain the target concentration of 1 g itraconazole/100 ml, the concentration of the marketed itraconazole formulation Sporanox® (Janssen Pharmaceutica). Therefore, we compared two preparation methods: the classical and the dissolving method to investigate if the method of preparation can have an influence on the solubility of itraconazole complexed with cyclodextrin (CD). With the classical method, the active compound and the CDs are jointly dissolved with a co-solvent, propylene glycol, in water. With the dissolving method, the active compound is first dissolved separately in a solvent in which it dissolves well, while the CDs are dissolved in water, before mixing. Three different CDs were used and compared for their complexing capacity with itraconazole. The complex formation of itraconazole with HP-β-CD, sulfobutylether-7-β-cyclodextrin (SBE-7-β-CD) and maltosyl-β-cyclodextrin (malt-β-CD) was investigated at pH 2, in the presence of 10% propylene glycol for an oral solution. These three CDs were chosen as they can also serve in formulations for parenteral use. The method of preparation had an important influence on the complex formation. With the dissolving method, a much higher solubility of itraconazole was obtained using the same CD concentration than with the classical method. Inclusion capacity obtained with the dissolving method was comparable for HP-β-CD and SBE-7-β-CD: 1 g itraconazole/100 ml of 25% HP-β-CD or of 30% SBE-7-β-CD. In 100 ml of 40% malt-β-CD only about 500 mg of itraconazole could be dissolved. With the classical method only around 160 mg itraconazole could be dissolved with 100 ml 40 % HP-β-CD or SBE-7-β-CD. Due to the fast preparation, once the CD amount is known by pretests, the dissolving method shows also an advantage for industrial production.