The paper discusses the relationship between city and war, from antiquity to modern conflicts. The permanence of the connection was especially emphasized with the metamorphoses in the appearance of the city caused by the war were also recognized, as well as the restrictions that the city places on military power. Dependence of the commander’s decisions on the specifics of urban warfare was considered. It was concluded that commander’s decisions always fall into the plane that passes through three points: imperative of victory, principle of avoiding unnecessary risk and moral conscience. In most cases, commanders have to balance between them considering many factors – political, sociological, economic, psychological and ethical.