Originally Posted by
MP2086
I probably was too general in my question. The friendly debate was more along the lines of "If MDW had TSA and ORD didn't, which would you fly and how much of a premium would pay to do so?" The underlying assumptions are that you still have to show an ID to fly, and your luggage can be searched, but it's at the airline's discretion, just like a private FBO.
I think that the risk potential is such that either choice will give similar results.