Disclosed are systems and methods for generating recommendations to users based on historical travel information and electronic communication data. The disclosed systems and methods provide a novel framework for automating the transmission of electronic travel-related recommendations to users by consistently monitoring electronic messages received at an electronic communication mailbox corresponding to a user. The disclosed framework operates by leveraging historical user data, data parsed from electronic communication mailbox corresponding to a user, or various vendor information, and using the aforementioned data as inputs for travel-related recommendation models, in order to generate and transmit the optimal travel-related recommendations to a user.