A small U/V combo aimed at the Willis (fka Sears) Tower should suffice. You probably don't need any amplification unless you have a very extensive signal distribution system.
WBBM's main programming is available on their channel 26 translator, probably doesn't reach you. Alternatively, their main programming is now carried as sub-channels on WMEU, UHF channel 32, which your report indicates should be easily received on any non-compromised UHF antenna making high-VHF reception irrelevant.
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