South and North Korea, the divided nations on the Korean peninsula, began with the same modern city planning system, but following the adoption of different national ideologies—capitalism and socialism—, they established their own city planning system and developed their cities accordingly. However, the process of planning and developing a joint city of Kaesong Industrial Complex (KIC) led to the recognition about the need to bridge the differences and prepare for future joint development. This study examines North Korea’s city planning system by comparing the two Koreas’ systems, and identify the characteristics of North Korea’s city planning system through a case analysis of the KIC. By comparing two cases, we found two distinct characteristics of North Korea’s. The one is a tool for realizing ideologies and maintaining national system. The other one is that it is ideology-oriented system for the supreme leader and party while South Korea has control-oriented system for the public. We analyze the KIC case based on four pillars: planning system, development system and procedure, master plan, and use behaviors. Result of analysis shows that in KIC there are many socialistic features as we mentioned above in terms of planning system, urban design & structure, and use behavior even though a private enterprise-Hyundai Asan, in South Korea led the whole process. This study is meaningful in that it identifies the specific characteristics of North Korea’s city planning focusing on the KIC and is expected to serve as a baseline material to set the future direction for North Korea’s development.