Surface active ionic liquids (SAILs) have attracted significant interest as promising substitutes for conventionally available surfactants owing to their exceptionally favorable physicochemical features. Herein, the aggregation behavior of SAIL choline oleate (SAIL[Cho][Ole]) in the presence and absence of naproxen (NAP) drug and its interaction with alcohol such as methanol, ethanol, 2-propanol and 1-butanol at different concentrations and temperatures have been investigated by conductivity method. For alcohol-water systems at a fixed temperature, the critical micelle concentration (CMC) at a specific temperature was found to increase in the presence of alcoholic media. Finally, numerous thermodynamic parameters like standard Gibbs free energy of micellization (Delta G degrees m), standard enthalpy (Delta H degrees m), and standard entropy of micellization (Delta S degrees m) were calculated as well as explained thoroughly. The obtained negative values of Delta G degrees m and Delta H degrees m indicate that micellization is spontaneous and exothermic, respectively. The molar heat capacity (Delta C0 ) was also evaluated as well as explained. m