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"Friend" eh? Uh, ok.
I would say if you picked SWA over UPS, you have a screw loose. Heee heee
Seriously though.....it depends on what your "friend" is looking for.
I was looking for as good of a chance of job security as possible in the airline industry......#1.
I was looking to not have to deal with passengers.....#2
Not commuting would be ideal but I was willing to make that sacrifice.
You really didn't want PAX to complain about your landings, right?
I'd probably pick Southwest. Chicago is a great town.