i have to be careful when i book to fly into Fayetteville, NC because there is a Fayetteville, AR that always comes up...
I imagine Jackson MS (JAN) and Jackson County MI (JXN)could be a source of confusion, especially since half the country thinks MI is the Mississippi postal abbreviation.
I know for a fact that many many people coming to Bloomington IL (BMI) or Bloomington IN (BLM) wind up in the wrong place. Even some instances of entertainers flying to concerts at Illinois State U or Indiana U.
Years ago I flew to BMI on, I think, AirTran or TTA or something and they tagged my luggage to BLM. I pointed this out to the agent who told me not to worry - they don’t fly to BLM. Luggage made it home with no problem.
Attended a convention once in Vancouver, WA, just across the Columbia from Portland. Came time for the keynote speech, no keynote speaker.
He’d booked to Vancouver, BC, and was still driving his rental car.