This paper first introduces the concept of image as a key factor in recognition, and city identity as the dominant image of a region which is commonly possessed by individuals living and working in the region. Then, the new approach toward planning, the notion of self-organization associated with images and positive feedback mechanisms in terms of city vitalization, is discussed. Thirdly, carrying out the case study of a process in which Iida City in Japan has acquired a city identity as a puppet drama town, we present four stages in planning for city identity four stages and discuss the phenomena of city image self-organization. Finally, it is pointed out that multimedia are effective measures for the promotion of self-organization of city images, and that the role of local governments is very important in city planning to support the self-organization of cities.