My boyfriend Scott & I went on a dive trip in Cozumel over New Year. We flew out of Madison (MSN) & connected Chicago-O'Hare (ORD).
After we arrived at the airport & got into the terminal I slipped out of my flip-flops & put them in my carry-on. We checked in, then headed for the TSA check-point, where Scott took off his & put them in his bag. On a side note Scott had started going barefoot with me shortly after we started dating, but that's another story.
We got through security, then went to the gate area. While we got a few looks walking through the terminal no one said anything to us. We boarded & took off also with no problems, & during the layover of a couple hours we walked barefoot around the O'Hare terminal, also with no problems. The only comments were from a barrista at one of the Starbucks who asked us if we had forgotten our shoes & weren't our feet cold.
We boarded for the second leg of the flight, deplaned in Cozumel, went through Mexican customs & immigration, all barefoot & again no problems. We had a wonderful trip, living in swimsuits & bare feet.
The crowning event came a couple days before we left when Scott proposed to me, but that's also another story!