Glen Clark and I discussed the very topic about WLS TLs and APPs.
One thing they probably wouldn't be required to do is reduce power at Night if they moved further North. All other things being the same, the contours would pull in slightly due to the new skywave model. The skywave signal contours would also be pushed North into Canada, where it wouldn't matter.
WLS History Card. TLs on Second Card. Addison TL APP and another were on other pages. And yes, for a short time very early on, they broadcast from near Crete, IL.
Other strange sounding early TLs of Midwest area stations include WJJD Mooseheart, IL and WJR Sylvan Lake, MI.