The article is devoted to the issues of determining the attractiveness of large Russian cities for residents, entrepreneurs and tourism, as well as the factors that determine it. In view of this, the parameters of the socio-economic development in the cities with population over 100 thousand people are considered. Assessment of the cities’ attractiveness for the population implied an analyzing: the number of the settlement’s inhabitants, the level of wages, the level of crime, the provision of housing and doctors, as well as the magnitude of migration growth. As part of assessing the attractiveness of the cities for entrepreneurs, the volume of shipments of goods of their own production and the provision of services on their own, retail trade turnover, the level of employment, the availability and degree of depreciation of fixed assets, the number of residents, and the volume of investments in fixed assets were taken into account. From the standpoint of the forming tourist flows, the number of persons accommodated in collective accommodation facilities, the number of places in collective accommodation facilities, and the average number of employees in collective accommodation facilities were considered. On the basis of the study, a number of regression equations were formed, and an analysis of variance was carried out. At the same time, the assessment of the attractiveness of the territory from the point of view of tourists was carried out, inter alia, on the basis of the number of relevant requests on the Internet. Five groups of cities were identified, which are characterized by a specific ratio between the number of persons accommodated in the CSW and the number of Internet requests. The corresponding mathematical formalization of these relations is carried out. The proposed models of the attractiveness of cities complement each other and make it possible to implement an integrated approach to solving this problem. It is shown that the improvement of the situation, both in individual regions and in the country as a whole, is possible only through integrated socio-economic development, that is, through the use of indirect measures and the creation of favorable conditions for the formation of positive changes.