[JoeAZ]

Quotes from Rabbit 73:

"Your goal will be difficult to achieve. Your local signals are much stronger than the signals from Rockford and Milwaukee. You will need a preamp for Rockford and Milwaukee, but it would be overloaded by your local channels.
Also, your antenna should be aimed at the transmitters, so you would need a rotator or separate antennas."

"My advice is to keep your system simple and stick with the locals with your CS2MAX in the attic or outside."

"You can, at a later date, add a second antenna and preamp to experiment with Rockford and Milwaukee."

I agree 110% with rabbit73. A few points to consider. You will need to
get above the treeline if you plan to receive Milwaukee and/or Rockford.
That means an expensive tower or telescoping mast most likely. You are
correct to observe that analog and digital propagation are different.
Generally, analog coverage was larger than digital. What was, back in
the old days and what is, today, are very, very different. Get your
local, Chicago stations with your antenna mounted outside first. By the
way, you can stream Milwaukee news and possibly Rockford with
a Roku. Roku has free nationwide streaming of many, many stations live
newscasts. That would certainly be less expensive and more reliable.