A computer implemented method, data processing system, and computer program product for scheduling calendaring entries within the context of an instant messaging client. The instant messaging client receives input from a user to schedule an instant messaging chat session with one or more invitees, wherein the one or more invitees are selected from a list of contacts in the instant messaging client. The instant messaging client provides a scheduling interface to the user, wherein the scheduling interface allows the user to define properties for the instant messaging chat session. Responsive to receiving user input defining the instant messaging chat session, an entry is created in the user's calendaring system to form a scheduled instant messaging chat session, wherein the entry is based on the properties defined in the scheduling interface.