The article makes theoretical reflections and analogies of urban systems (ideal, functional, intelligent city) with human spirituality and spirituality of the city. The study considers spirituality as part of human comfort, and the need for urban spirituality as a key requirement of urban planning. The spiritual component is underestimated by society, as well as by specialists in organizing the space of social activity, while it is the intangible and vernacular that create the "face" of cities. The key idea of the study is that the city should be spiritually comfortable, and in substantiating architectural and urban planning decisions in today's dynamic conditions, spiritual criteria and categories of faith, culture, mentality should be the main ones. The phenomenon of spirit and comfort of cities has been reconsidered, approaches to returning spirituality to cities, wider participation of free human will (libera voluntas) in the process of their creation, deformalization of the existing practice of urban planning, activation of internal resources of people in the design of cities, formation of new forms of urban life and activity have been substantiated. Rethinking urbanization, we consider spirituality as an integral part of human nature and urban community, urban lifestyles and activities.
 A research methodology based on the provisions of behavioral psychology and cultivating the integrity of "reading, imaging and building a city" is presented. An approach based on the assertion that urban spirituality is realized through innate needs, challenges and contexts is applied. In the process of research, to build a model of spiritual comfort of the city, the position of the five-dimensionality of urban planning space (person – functions – conditions – geometry – time) was used and semi-structured interviews (surveys and conversations) were conducted with civil servants, persons who worked in the field of urban planning, management and religious affairs, as well as in institutional groups (creative unions, public associations, religious congregations, schools, families). This contributed to the collective assessment of this phenomenon, its connection with the city. Events and spiritual places that create a sense of spiritual comfort — coziness, calm and educate a person — are allocated, spirituality and sacredness of the city space as a system are analyzed. Proposals are formulated and architectural and town-planning recommendations are presented to strengthen the spirit and spiritual comfort of cities.