W..
I would say you look at the cost of the tickets WITHOUT getting the credit card offer.
So, basically you are saying you would pay $486. for your round trip ticket ($208 + $208 + $70).
So, if you can get the tickets for LESS than $486 but MORE than $416 (the cost of the round trip without the credit card offer) you SHOULD NOT do the credit card offer.
If you can't get the tickets for less than $486, then get the card, use the tickets and just make sure you pay off the card and cancel it within one year so you are not charged a 2nd annual fee. If you have the card for a 2nd year, the cost of your tickets just jumped from $486 to $556).
Make Sense?
I would NEVER have a credit card with an annual fee, unless it was a SUPER low interest rate. Then you would need to calcuate how much you are generally charged in interest to determine which is the better deal. probably this southwest card is a high interest rate card (special offer cards usually are).
Oh - wait. You might be saying if you get the credit card you would then get 2 FREE tickets at the wanna get away price up to $208? Then...... that's different. Because you would be getting the tickets for free.
Again - it depends on your credit card usuage. if you are going to carry a balance on a high interest credit card with an annual fee you will more than double the cost you pay for the tickets in a small amount of time.... so, not worth it.
If you can get the card, get the free tickets, use the card and cancel within a year then it might be worth it. That's a lot of administrative hassle, though.
Good Luck and have fun on your trip.