Originally Posted by
NotHamSarnie
This has never been a feature for iCal - I always have to go to Manage Your Trip and click on the sidebar to get the emails (one per leg, very annoying) with the .ics files to import (one by one, tedious) into my calendar. You can choose to do the same for Outlook calendar - not as convenient as getting it automatically for sure, but a solution nonetheless.
For a long time, my iCal added upcoming flights automatically (believe it's a Siri function) and has not been working recently similar to the OP. Not sure what changed either on the AA end of things or with my Apple products but the function doesn't seem to be working any longer.