As far as Chicago is concerned, some signals are within reach if you use a large high gain antenna. I'm thinking a Winegard HD9095P or an Antennas Direct 91XG equipped with the Antennas Direct CPA-19 preamp.
The 9095 claims 16 dBd gain at CH-32. When I estimate the net NM of the signal from WFLD-Fox I get a good number, +10.5 dB. (see attached)
Can you mount higher? If so, it would be interesting to see a TV Fool report for 40' or even 60'.
I would cable the 'Chicago' antenna separately. There are a variety of ways to connect multiple antennas, perhaps the simplest and least expensive is an A/B switch. Here are some other ideas:
http://forum.tvfool.com/showthread.php?t=2882
http://forum.tvfool.com/showthread.php?t=820