Based on some research I did today, and possibly the reason they can’t replicate is because I think it only happens with the MS Marketplace version. It’s the same version as they use but I’m sure there’s something Microsoft may do to marketplace files that’s causing the issues.
If you uninstall it in the content manager, and then load into Chicago it works. If you reinstall it and load into Chicago without closing the sim it works. The moment you exit the sim and restart it and try to load into Chicago, boom it freezes. Just thought it was worth noting what happened on my end when researching. Note I do use FSDT KORD. I tried uninstalling it and just loading in with Chicago and I had the same issue.
I only started having this issue after Sim Update 5 and have no problems flying into Chicago. The issue only arises when trying to load straight in from the main menu.