Kllrbee,
You got some really good suggestions from teleview and StephanieS. If I lived where you live, I would go somewhere between their suggestions.
There is a VHF-low station in the Milwaukee group, so an all channel antenna (HD1800, HD1850, or HD7084P) would be good to point at 29 degrees magnetic.
Chicago mainly has UHF stations, so a DB8e would be a good option pointed at 143 magnetic, unless you want CBS from Chicago, in which case you could add an Y10-7-13 pointed at 143 magnetic.
I would get 2 RCA TVPRAMP1R s, one for each group of channels. For the Milwaukee group, I would connect the all channel antenna to the combined input on one preamp. For the Chicago group I would put the DB8e into the UHF input on the other preamp and if you get one, a Y10-7-13 into the VHF input.
I think the RCA TVPRAMP1R is the best value for preamps right now. It is the least expensive dual input preamp. From compiling other people’s experiences I think it might have a 1dB better noise figure than the new 7778. (I have not done any experiments of my own, so me saying the TVPRAMP1R may be lower noise comes from reading manufactures claims, reading forum posts about multiple preamplifiers, and doing some excel “desk jockey” work.)
From where you are, you “may” have an option to do a single cable solution for two antenna systems. The Milwaukee group is very close to 90 degrees from the Chicago group. The antennas suggested so far in the thread have nulls at 90 degrees. If the groups were exactly 90 degrees apart and you had LOS signals, I would be more confident in what I am about to suggest, but it would be inexpensive to try.
When everything is hooked up, if you go with 2 antenna systems, you will have a point where you have a power inserter going to the Milwaukee antenna and a power inserter going to the Chicago antenna(s). First do a channel scan for each antenna system (one hooked up to the TV at a time) and note what channels you get. Then connect the output (to tv) line from each power inserter into a splitter backward to use it as a combiner, and take the combined out and connect it to your TV and do a channel scan. If all the channels are there, it worked, if not, replace the splitter/combiner with an AB switch.
The reason that may work is if one group of station hits a null on the antenna for the other group of stations, when they get mixed together in the combiner, no signal from the wrong stations will come in one antenna messing up the signal from the right antenna. As stated above, that would be more likely to work with stations 90 degrees apart and a LOS path to prevent multipath doing who knows what to where the signals come from.
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