I never quite understood why they went into ORD in the first place. Anywhere they flew was going to be head to head against both/either AA and/or UA except for DAL/HOU instead of DFW/IAH.

I was a frequent traveler on MDW-IAD before WN went into DCA. And IAD was actually more convenient than BWI for visiting clients in MDT because there was less traffic on US 15. But DCA made it superfluous without travel from secondary West Coast cities which UA might not have wanted to serve.