This is another sad day for AM Radio and Radio in general. This will indeed create worse signals in outlying areas, and a lot more fading.
Good for radio hobbyists who still have crystal radios in the NWC/ORD area. You'll likely pick the signals up on the wire that clips to the antenna. Hard to not hear two signals at the same time though, without some tuned RF filters.
WLEY 107.9 will have to move too. And with the newer Section 73.213 rules, that could be problematic. It's already DA, and would likely have to downgrade, and the Boosters might be affected.
WLS 890 should move to diplex with WGN. THAT would be an improvement. The Northern Chicago city and suburbs get a very weak signal by today's standards, and it has to hurt the ratings. WDLS 900 Wisconsin Dells would be the only station that would be problematic. WSNQ and WFRO are gone from 900. Dave Magnum is a good committed radio owner, and there's a translator, so I don't know if he would want to sell it or downgrade it. WLS tried to move to Addison in the 1970s, and that was a problem, according to the late great Glen Clark. The 900s are Class D, and CHML doesn't have to be protected at Night like a US Class B station would.
BTW, WIND only moved a quarter mile or so in 1975. They have an AUX at the Des Plaines site, which would meet all the main facility rules, but it's only 1000 watts Day, 580 watts Night, nondirectional.