You've got AA and UA - that go direct - if you can't get on the direct ones because they do fill up frequently, look at the AE flights that fly DFW-outstation and the outstation-ORD flights.
True, true. If you can hold out for the 777 run in the early afternoons, it's generally open. The rest of the schedule on AA is generally overbooked and jumpseats are filled.
Add to that, if there's a cancellation for whatever reason now it's a real bit*h. I've only experienced that once, but I wasn't commuting so I just went home and waited until the next day. Otherwise (as an AE employee) I haven't had many troubles. I go on United a lot too (ie no non-rev charges). ATA and AirTran go in to MDW as well... That would work in a pinch taking the Orange Line and transferring to the Blue Line downtown, but you're looking at about 1.5 hrs on the L)
You're not mentioning all the advantages of 1.5 hours on the L train! For $1.75 you get all the following.
-Chiropractic technique... while sitting in your plastic chair, you're likely to have your neck/back cracked at least 3 times from the abrubt movements.
-Ability to save your soul... with only $1 donation to your rosy smelling bum that conveniently hops from car to car asking for help. WWJD?
-Wear your uniform for stare-bots. Help out the local population with nothing to look at during those long tunnels. You and your fancy pilot getup will allow their gazes to land on you. (Attractive females not included)
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