There's a known problem with MSFS which results in airports crashing with add-on liveries IF the airport includes airline code ( which change the composition of AI landing there ).
The latest version of KORD, which you should have if you ran the FSDT Live Update, doesn't have any airline codes anymore, and this seems to fix all crashes but, we cannot be absolutely sure if a "bad AI" can still cause problems because, it's not as if with no airline code the bad AI cannot come, they might just come at different times.
In any case, the problem it's confirmed to be caused by bad AI ( missing or corrupted textures ), there are some very bad AI liveries sets around, we checked some of them, and within minutes I could find many illegal .DDS, several of them cannot be even opened with an external utility like IRFanView, which crashes too.
So, again, the problem doesn't have anything to do with the airport itself, we can only reduce it a bit by changing or removing airline codes from parking spots, but the real solution is fixing the AIs, which surely we cannot do ourselves.
Also, we notified Asobo about this, they should be able to check, and possibly made the sim less prone to crashing when used with AI with missing/corrupted/illegal textures.
