I was going to PM you to get your advice on parking at Midway!! DH is coming down for the last 4 days of our trip so he will parking rather than using a car service. We have never parked there before so do you have any recommendations?
Now that he has decided to come (his first time EVER in the summer) that will DEFINITELY be the week of the Stanley Cup!

DS and I were down there last time they won it, so I was grateful that it was on NBC so I could see it.
It's been a fun season to watch, especially since, for awhile, it really looked like there wouldn't even be a season...
ON TOPIC:
As for the SWA prices out of Midway, they are definitely higher this year than I have had in the past, but still way better than the legacy carriers and their luggage fees. We travel midweek, almost exclusively, and I am paying $111 each way (when I can normally get it for $85-$95). I can't touch a legacy fare for under $250 roundtrip out of Midway or O'Hare, plus I would still have luggage fees.
The key to SW is patience. (I know, not an easy feat!!

) I check my airfares daily. I also keep an eye on earlier month's fares, especially when the sales are happening, to give me a rough idea about how low I can expect them to go. I know for some markets, its best to buy the day they release. I have never found that to be the case with Chicago/Midway. They are sometimes almost double what they should be