Getting onto a SW flight with no boarding pass. 
http://www.foxnews.com/us/2014/08/07/san-jose-to-los-angeles-stowaway-had-mental-treatment-history-trying-to-board/
Best line: "I don't think it's wise to say why I got through. I don't want to help the enemy. I'm first and foremost an American," she said.
A friend of mine's father travels to a certain city weekly for business and he had a crazy story recently:
This guy flies back home every Friday (very short flight) with JetBlue. On that particular day they were pushing back his scheduled flight to NYC by a bunch of hours. He canceled that flight and got on a flight to PHL, intending to drive from their back to NYC in time for Shabbos. As they're pulling away from the terminal, his wife calls him and tells him his original flight to NYC is back to its originally scheduled time. He more or less fakes a panic attack and forces them to let him off (requiring an agent to escort him across the tarmac).
He runs to board the JetBlue flight, but doesn't have a new ticket yet (for whatever reason they were having trouble getting it reticketed). Incredibly, the scanner at that gate was broken and they were checking boarding passes manually, so he pulls out his original boarding pass and gets on the plane. He sees someone in his original seat already, so he just finds an empty seat (flight was nowhere near full) and flies home just like that.
He's still figuring out if/what he's halachically required to pay JetBlue, and how to go about doing that. All I can say is thank G-d my regular commute doesn't involve an airplane.
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