$500 is not bad from the midwest, considering it has been around $700 for over a year. ORD, STL, IND, MSP have all been high lately. If you are waiting for $300, you may be waiting a while, although you just never know if a sale is going to pop up. We jumped on those $258 sales on Delta back in October for our June trip, but that is the cheapest I have ever seen (and yes, we are kicking ourselves for not buying for more than one trip).
I sent you a PM.