Abstract: The present invention is directed to a method, computer program, and system for automating the planning, reserving, and purchasing of travel accommodations based on calendar events of a user. A user's event list is created on an application server, which may comprise synchronizing a calendar in at least one embodiment, and a user's booking request is received at the application server for a selected event in the event list. Additional information is then retrieved by an event booking component, and along with the received user's booking request, allows the event booking component to generate at least one travel plan for the user. The travel plan is then reviewed and selected by the user, and then fulfilled by the application server.