This article focuses on the influence of the structural elements and the dominant realities within the international system on the emergence, nature, and functioning of the regional structures composed of state and non-state actors. Examined through a comparative analysis of the international conjunctures, since the emergence of regionalism in the modern sense, the impact of the wider context defined by the polarity and the secondary factors, like security considerations, détente, economic concerns, and globalization on the actors’ behaviors related to the regionalization movements would be at the center of this study. The regionalist movements that have gradually accelerated since the last years of the twentieth century have appeared as significant cooperative elements of international affairs. The most recent trend characterized by the rise of the protectionist walls of the nation-state has again placed these movements at the center of the debate. Particularly, the examination of the substantial impact of both the structural and conceptional transformations appeared in the post-Cold War period on the actors’ regionalist tendencies would make the influence of futures changes in this sense.