Background: The International Civil Aviation Organization (ICAO) is a “Club” of sovereign States. ICAO is a specialised United Nations agency (UN) with 193 Member States. If a dispute between these States and the diplomatic channels does not find a mutual solution, disagreement arises; however, the ICAO Council has an essential function in settling disputes. This settlement procedure is structured under the Chicago Convention (1944), the Rules for the Settlement of Differences (1957) and the Rules of Procedure for the Council (1969). However, Member States do not welcome these provisions, demonstrated by the scarcity of dispute settlement procedures before the ICAO Council in the last 80 years. This article introduces these legal disputes and looks for justifications based on the nature of the cases. The Council is a unique permanent body within ICAO. Although ICAO in the former century became rather a political (diplomatic) body upon its foundation, that is why the absence of successfully concluded dispute resolutions is a legal viewpoint that is more than interesting. This research paper reveals examples of the lack of effectiveness of the ICAO Council’s dispute settlement, focusing on the nature of the State’s interests and the outcomes of the procedure, furthermore, the role in these disputes in front of the International Court of Justice (ICJ) or arbitration. Methods: This article focuses on understanding and analysing the historical context, international cooperation and diplomacy, and the regulatory landscape of dispute resolutions and settlements. The search was based on databases, academic journals, and official publications from aviation authorities and organisations such as ICAO. The research utilised qualitative and quantitative methods based on empirical observations and examinations (document analysis and case studies). Results and conclusions: The ICAO Council has rule-making, judicial and administrative functions. It is a quasi-judicial body, and its President has the authority to settle disputes among the contracting States. However, if we look at the history, in the last 80 years, only 10 cases were handled by the ICAO Council. The main reason for the lack of ICAO Council dispute settlement decisions is the growing diplomatic (political) function of the ICAO Council. Aviation is a crucial commercial activity for every State, meaning the aviation industry is determined by political interests and decisions. Such political interests and subtle international relations often prevent States from submitting themselves to binding legal procedures. Another reason for fewer disputes before the ICAO Council is the need for more provisions and rules to support transparent and legally binding decisions. The current rules are neither appropriate nor comprehensive enough and cannot be executed in the same manner as court decisions. In addition, the ICAO Council’s decision can be appealed to non-ICAO bodies such as the International Court of Justice. Therefore, it is highly recommended that the whole processual mechanism be revised or that a new, dedicated judicial body with clear legal status, jurisdiction, and competence for dispute resolutions be created.