The "new" tower for WBBM is more efficient. It produces the equivalent of 50 kw from the old tower.
Except for differences based on individual listener distances from the old and new sites, there should be no difference in signal strength in the service area.
Agree in part, disagree in part.
The really smart AM engineers I know (because that ain't me) tell me to expect some real-world effects at the edges of the market because the taller tower will produce a different vertical takeoff angle for the skywave - which will mean the groundwave-skywave cancellation ring will move (closer to Chicago, IIRC).
Also, the really smart AM engineers I know tell me, and not with much pleasure, that most of their domestic workload these days consists of telling old-line AM owners whether it's feasible to move away from their legacy sites to locations where the land is less valuable. Which is to say, we'll be seeing more moves like this - and probably more along the lines of WMAL (which will significantly impair the in-market signal, especially at night) than WBBM (where you'll have to look really hard to notice a change.)