A deep eutectic solvent (DES) is a mixture of two or more chemicals that interact via hydrogen bonding and has a melting point far below that of the individual components. DESs have been proposed as alternative solvents for poorly soluble active pharmaceutical ingredients (API). In this study, the solvation capacities of six deep eutectic solvents were compared to water and three conventional pharmaceutical solvents (PEG 300, ethanol and glycerol) for 11 APIs. The experimentally determined solubilities were compared to computational solubilities predicted by the Conductor-like Screening Model for Real Solvents (COSMO-RS). While the conventional pharmaceutical solvents PEG 300 and ethanol were the best solvents for the majority of the studied APIs, API-DES combinations were identified, which exceeded the API solubility found in the conventional pharmaceutical solvents. Furthermore, it was also possible to obtain high solubilities in the DESs relative to water, suggesting DESs to be potential solvents for poorly water soluble APIs. In addition, the relative increase in solubility found in the experimental data could be well predicted ab initio using COSMO-RS. Hence, COSMO-RS may in the future be used to reduce the experimental screening of potential DESs for a given API.