The rapid integration of Artificial Intelligence (AI) tools, specifically text-to-image generators, across various domains has had a profound impact on numerous fields. Despite this, the potential applications of AI image generators in architectural education, particularly in teaching the history of architecture, remain underexplored. This research aims to uncover the possibilities of utilizing AI image generators, with a specific focus on the capabilities of Leonardo AI, to enhance communication and engagement. This study employed an experimental methodology to investigate how the integration of AI image generators in education on the subject of “History of Architecture” promises to elevate the learning experience, offering new perspectives, visualizations, and interactive tools. Two workshops were conducted with university students to explore AI image generators’ potential applications in architectural history education. The first workshop utilized an iterative approach, while the second aimed to assess students’ analytical skills. The ultimate objective was to determine the capabilities of this tool and stimulate discussions regarding its potential future implementations. Following the workshops, online questionnaires were administered to students, and interviews were conducted with educators. The findings of this research underscore the need for validating AI-generated images, establishing guidelines to prevent misuse, and designing tailored AI tools for History of Architecture courses, thereby paving the way for further advancements in architectural history education.