Hey Andy, I would recommend disabling any addons and see if the issue persists.
I'm assuming Chicago O'Hare is an addon from FScloudport? Can't remember if Airport is default IPACs or part of Orbx Meigs addon?
If issue still persists, delete the .TM log before restarting sim, then try to replicate the same scenery that causes issue. If sim crashes, it should be
picked up by TM log to which should explain whats happening