Information and communication technology is changing the manner in which urban policies are designed. Saudi Arabia bases its smart initiative on the use of information and communication technologies in six dimensions, including economy, people, environment, living, mobility, and governance to improve quality of life and sustainable environment. This study draws on four Saudi Arabian cities including Riyadh, Makkah, Jeddah, and Medina, and aims to analyze their progress in the transformation into smart cities. The six identified areas were assessed using 57 indicators based on national and international information and literature. The results show that the four cities are progressing successfully into smart cities, with the highest progress evident for smart economy and the lowest progress for smart mobility in all investigated cities. Study findings show that Riyadh has made the most progress in the six smart city dimensions, concluding that Riyadh has been efficiently executing the smart city initiative with an aim to be a unique model in the world.