I think 'deep fringe' may be a bit pessimistic, but I'll agree that 'fringe' is an appropriate word to use here. The majority of the signals from Chicago are within reach.
Option 1) A Winegard HD7698P and Antennas Direct CPA-18, roof or tower mounted, aimed at Chicago (331° compass). This should give you all the Chicago signals on your report with double digit NM predictions. No chance of seeing WOCK, real CH-4 and some of the Chicago signals with single digit NM predictions.
Option 2) A Winegard HD8200U and Antennas Direct CPA-18, roof or tower mounted, aimed at Chicago (331° compass). This should give you all the Chicago signals on your report with double digit NM predictions. A chance of seeing WOCK, real CH-4 though I believe your chance of reliable reception would be 'on the edge, with toes hanging over'. There would be a slightly lower chance at reliably seeing some of the Chicago signals with single digit NM predictions.
With both options, I think you could improve reliability of reception if you could safely mount higher. You can always run additional TV Fool reports at higher mounting elevations to see if signal conditions warrant the extra work and expense.
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