In recent years, much attention has been given to the current situation and trend regarding economic development in the Democratic People’s Republic of Korea (DPRK), of which urbanization is an important indicator. In the present study, (i) the urbanized area is estimated using DMSP/OLS and NPP/VIIRS, (ii) the current spatial pattern and the change characteristics of typical cities are revealed, and (iii) the scale and developmental stage of major cities in the DPRK are judged through comparison. Although the DPRK is relatively closed, the financial crisis in 2008 indirectly affected its economic development, and a large gap remains between the urbanization level of the DPRK and that of China and the Republic of Korea. The large cities in the DPRK are located mainly in its eastern coastal areas and western plains, and there has been no significant expansion in Pyongyang, Chungjin, and Hamhung in the past 28 years. Although economic construction has begun again recently in the DPRK, further reform and opening are required. As the DPRK’s relations with its neighbors and countries around the world improve, its economic development and urban construction will present a new pattern.