Originally Posted by
Flyingggggggggggg
TripIt (I can't bulk-add flights to TripIt, it's just as one-at-a-time as Flighty)
As you mentioned you were comfortable creating calendar items programmatically... have you ever looked at using
https://tripit.github.io/api/doc/v1/...method_create? It's provided by TripIt themselves and although it's poorly maintained (understatement!) it sort of works.
I only use the TripIt API to pull my data out but can't see why you couldn't use it to add flights in bulk.