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Southwest Gave Me a $300 Chicago Vacation. Here’s How It Happened

Southwest flight with wheels down.

It was 5:30 pm. Sleep was a distant memory, with my bed in Kuala Lumpur, Malaysia, being the last place I had slept. That was nearly 40 hours ago. Boarding was starting at Chicago O’Hare International Airport for my second to last of five flights. I was ready. Unfortunately, my pilot wasn’t. Shortly before boarding, …

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