Abstract: This study compares the abilities of two AI chatbots, OpenAI ChatGPT and Google Bard, to understand urban environments, inspired by Kevin Lynch’s “Image of the City.” We examined their grasp of city landmarks, navigation, and spatial perception. ChatGPT offered factual, generalized responses, while Google Bard provided detailed, immersive answers with historical and cultural insights. Despite occasional navigation errors, both showed reliable knowledge of urban features. This research showcases their unique styles and potential to connect physical and digital worlds, offering insights for future AI development in urban planning.