Not myself, but I actually saw the Bloomington IN/IL problem happen to some folks! I was at a conference in Bloomington Indiana (which I can drive to) and a carload of folks arrived quite late for the conference because they had flown to Illinois. They didn't catch it until they piled into the rental car, plugged the conference hotel address into the GPS, and it told them it was a 4+ hour drive. they went back up to the rental car counter, "uh, is this thing right?"

I also have some friends who went to the airport (STL) with the intent to just pick a flight when they got there...just jump on a plane for a destination they would choose in the moment (this was decades ago). They saw "Ontario, CA" on the board and thought, "great, Canada will be fun". Imagine their surprise when they got off the plane and they were in Ontario California.

My cousin just told me that last week he was boarding a commuter flight (somewhere) that had two flights boarding at the same time at the same gate to different destinations. Even though it was announced multiple times, once on board several people had to get off one plane and onto another before they could leave.