2011 marks the 90th anniversary of the famous resolution on what is now known as the Åland Islands Question. The League of Nations mediated between Finland and Sweden (1917-1921), eventually reaching a compromise establishing Åland’s autonomy with its unique Swedish character, demilitarization and neutralization. Statistics shows that it is the oldest and one of the best-functioning autonomies in the world, and is widely used as an inspiration in international conflict resolution. This paper will explore the historical background and special characteristics of Åland autonomy, considered by many experts as an example of a successful and enduring solution to ethno-territorial conflict. Certain features of this autonomy might be applicable to the future status of the Nagorno-Karabakh region within the framework of the resolution of the Armenian-Azerbaijani conflict, which makes this research especially significant.