Originally Posted by
himavant
I'll be flying OAK (Oakland) <-> MDW (Midway), non-stops every week.
I live in Oakland and fly to Chicago to be there Friday afternoon and all of Saturday. I have to arrive in Chicago before 1pm every Friday. I have to fly back to Oakland anytime after 6:30pm on Saturday.
Southwest might actually make the most sense in that situation. However, let's look at other options, as a thought exercise, if nothing else.
You could fly out of SFO on United or American. Both have high frequencies to ORD. The primary advantage would be elite status. You'd be flying over 80k miles in 6 months. That's almost enough for top tier elite status on either one.
On your route, the major benefit would be upgrades. However, it's a difficult route to upgrade. Optimistically, you could be sitting in first class half the time. Also, with elite bonuses, you'd easily have enough redeemable miles for a business class ticket pretty much anywhere in the world, or probably 5 coach tickets on your SFO-ORD route. (This compares to what is, essentially, a 10% rebate from Southwest - with bonuses, it's probably close to 4 round trips on OAK-MDW)
So the question - is the better inflight experience of first class plus much better miles redemption options worth crossing the bay?
(Other comments: Virgin America is also an option but their frequent flyer program is terrible. And on the subject of cost: the OAK-MDW route fluctuates quite a lot, especially on Fridays. Are you sure it's realistic to expect $175 each time?)