The article describes the evolution of the urban settlement of the Kaliningrad Region, examined the structure and characteristics of the landscape environment of the cities of the region, analyzed their natural and anthropogenic components, and proposed a methodology for assessing the quality of the urban environment according to the degree of their construction, using satellite information, and the degree of transport connectivity of Kaliningrad. The system of urban settlement of the Kaliningrad Region in general has been inherited since the time of East Prussia but has undergone significant changes related to changes in state and administrative borders, the change in the ethnic composition of the population, and the cardinal restructuring of the management system. In modern times, urban settlement is formed against the backdrop of modern socioeconomic and geopolitical processes associated with the exclave position of the region in the Russian Federation and the difficult economic situation in the country and in the world as a whole. Currently, there is one big city in the Kaliningrad Region – the regional center – around which the city agglomeration is formed. The remaining cities of the region are welterweight and small. The stability of the modern geodemographic situation is ensured by migration growth, and the small size of the region and the presence of good quality intra-regional transport infrastructure (roads and railways) ensure the stability of the population of cities remote from the center due to pendulum migrations.