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Use TVFool's Online Mapping tool in "Hybrid" view (turn on the lines, too) to experiment with potential tower or a mast locations to see what effect the trees to the north might have and what location it would take to achieve LOS to both cities. Avoid the trees if you wish to be assured of the highest probability of success.
There are multiple ways of addressing your situation, depending on your priorities and budget. A single, large antenna on a rotor is certainly one way to do it. Another would be to focus a large antenna on Chicago and a small one on Milwaukee and to use an A-B switch to select which antenna to use..
Unless you have to have WeatherNation out of Milwaukee or WOCK out of Chicago, there's no need for a large, all-channel antenna.
I'f you'd like to avoid the rotor/A-B switch and try a single-antenna setup, a 4-bay antenna aimed at Chicago should be able to get almost everything on your chart. Most likely, only WBBM out of Chicago would require additional attention if it is a priority. Milwaukee stations, including the lone VHF station, would likely be received well enough off the back to make it work.
You'll have to do some research on the mounting location above and consider the number of sets in the household along with the capabilities of all sets as to how they would handle a rotor/switch arrangement. Some tuners force the owner to do a complete re-scan (undesirable!), others permit keeping previous data and adding new, either manually or via a scan.
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