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This dissertation was written as a part of the MSc in e-Business and Digital Marketing at the International Hellenic University. The main goal of this dissertation is the choice of the features and the designing of a chatbot for Thessaloniki in the Travel industry. To select the features that the chatbot will have, the websites TripAdvisor, Booking, Airbnb and chatbots Robin Travel Bangkok, Robin Travel London, Robin Travel Taipei and Prago have been analyzed. Furthermore, for the purpose of this dissertation, a company named Enchatted with expertise in the field of evaluating bots, has provided me access to the professional version of Botsociety, to create a chatbot. Therefore, Botsociety and its capabilities were used to design the chatbot. I would like to thank my supervisors Pr. Ionnnis Magnisalis and the company Enchatted for their guidance and providing the appropriate tools for the purpose of this Dissertation.