Originally Posted by MDtR-Chicago

You didn't ask, but... are you sure this is what you want to do?

Depending on your exact situation, Southwest could either be incredible or terrible.

Compare a great experience:
45 one-way trips which are something like SFO-LAX - easy 1 hour in the air, great schedule on Southwest, etc.
And then, you'll use your points to redeem for similar trips, like maybe SFO-SAN for a weekend...

To a terrible experience:
45 one-way trips that are something excruciating, like MDW-PHX-ELP
And then, when you try to use your points, you realize all that flying might buy you a single ticket to Bali. In Coach. If you're lucky.

Why have you already decided to commit 6 months to Southwest and should we try to talk you out of it?