Perfect timing with the Delta announcement. I haven't taken Southwest in years but unless Delta maskes some esrious rollbacks to their announcements, I'm going to be a free agent and fly to chicago a lot.
Main drawback to using WN, even though I prefer Midway over ORD, is no lounge if there is a delay. WN will be getting a lot of my monthly chicago flights if this opens next year
Even if I do stick with Diamond with DL, it will be nice having the lounge since MDW is more convenient to the loop.