This paper presents an analysis of the dynamics of the evolution of multi-airport systems worldwide that can help to guide their effective development in the future. Given the capacity constraints on existing major airports, the development of multi-airport systems is going to be a key mechanism by which air transportation systems around the world will be able to meet future demand. In order to better understand how these systems will evolve, a systematic case study analysis of 59 airport systems worldwide was performed. The analysis showed significant differences in the evolution of multi-airport systems across world regions. In the United States and in Europe, the recent development of multi-airport systems primarily involved the emergence of secondary airports.