Sustainable development, smart waste management, and circular economy principles are paramount to the significant worldwide trend of smart city-related research and projects. The basic hypothesis of our research is that artificial intelligence (AI)-based IT applications have an increasingly important role in the field of smart cities in terms of issues related to waste management. In our present article, we set out to analyze the characteristics of chatbot applications dedicated to waste recycling in the case of smart cities and propose some innovative ideas to improve the efficiency of such applications. Based on the consultation and analysis of a whole series of chatbot-type applications used to facilitate the recycling activity, we systematically analyze and evaluate five illustrative examples of chatbots employed in the context of material recycling. We provide performance comparisons in a table based on specific relevant criteria. Furthermore, the detailed analysis of these chatbots has led to the idea of improving the performance of this type of application. In this sense, we propose a series of innovative concepts that can be successfully implemented in future chatbots dedicated to the field of the circular economy. Here, we detail the innovative ideas that can promote the circular economy and capitalize on the potential of chatbots in the waste recycling activity. We also identify some possible limitations of these new ideas that we propose to be implemented. As for future research directions, our goal is to develop a chatbot dedicated to improving waste recycling practices within the framework of a smart city. Such innovation holds promise in improving sustainability efforts and fostering environmental stewardship within urban environments.