Great thread!
For me, it's the Delta Shuttle, fall of 1997.
I remember how proud I was of myself as a college freshman I was able to convince mom and dad that flying home for Thanksgiving really was a better idea than taking the bus

Back in those days, they had a student pass? so it was really easy to just head down to Logan and jump on the next plane.
Of course my checked luggage consisted of my laundry bag.