Creativeness is not only the trademark of successful entrepreneurship in a business environment, but is also a necessary ingredient for success and achievement in a complex policy system. The urban environment is one of the places ‘par excellence’ where creative ideas and actions can flourish, if they are supported by smart policy. Urban planning is one of the multi-faceted constellations that have triggered an uninterrupted attention in the literature after World War II. It has in recent years put creativeness high on the strategic agenda. This paper aims to offer new perspectives for strategic development of an urban system, on the basis of creative knowledge management that should induce innovative investment developments in an urban setting. The ultimate goal would be to make the city more attractive and thereby to contribute to urban welfare as a multi-attribute policy objective. The conceptual framework of the paper is elucidated by presenting an empirical comparative case study on Italian urban areas, with a major interest in Caserta (in the Campania region in Italy). The analytical framework deployed in this paper is based on recent multi-criteria methods.