I remember hearing years back that MDW was Southwest's largest hub with a similar feeling of surprise, knowing that they were based in Dallas. Unlikely they will ever move though in the near future (as cool as it would be to have another airliner based in town). I'm pretty sure even the threat to move to Chicago over the Wright Amendment back in the day was more or less and empty threat, especially since leaving Texas would still not have solved the issue of flying across the country from Love Field, their primary base of operations in Texas (in addition to Hobby-Houston).
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"Eventually, I think Chicago will be the most beautiful great city left in the world." -Frank Lloyd Wright
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