The information technologies help solve the most difficult problems, qualitatively change the provided educational services and create conditions for comfortable living and development for each inhabitant in particular, and the city’s community as a whole. In the context of the implementation of these projects, the procedures for the selection and acquisition of a profession are important, taking into account the personal characteristics of applicants and the needs of the city’s community. The decision-making process for choosing a future specialty starts even while studying at school, and is actualized during the selection of external independent evaluation subjects. Another important step in this chain is the choice of an educational institution for further education and specialization. The paper proposes an information technology of personalized choice of profession in accordance with the needs of a person and the requirements of the labor market in a smart city, which is presented in the form of five consecutive functional stages: determination of professional inclinations and abilities; monitoring of the urban labor market; a choice of the future profession; a choice of educational institution; formation of an individual learning trajectory. The models and methods of information technology support of personalized choice of a profession are described, in particular: model of data analysis for determination of professional inclinations and abilities of a person on the basis of the results of vocational guidance tests have been developed, which made it possible to optimize the process of determining the professional peculiarities of a person; the methods of monitoring the labor market of the city; using the methodology of constructing data hypercube, the method of analysis of educational activity in educational institutions in the city acquires the further development. The main characteristics of the developed one-page information technology web application are presented which combines all stages of training specialists in a holistic system taking into account the needs of a person and the requirements of the labor market in a large city.