If we're looking at the FM dial, bigfan suggested 95.5, which used to do okay as smooth jazz but has struggled with various Hispanic formats. Hubbard could conceivably part with 100.3, since they seem to shoot themselves in the foot with that station so as not to cannibalize the Mix, resulting in a soulless jukebox that is no things to no people. 94.3 is Christian now but could stand to cash out big;
their stick is out in the western burbs so they'd have strong coverage in those Key Demographics.
That's all I see that could be in play. CBS isn't going to sell to the competition so scratch five there, everything below 92 is reserved for non-commercial broadcasters, and anything else on the dial is either as solid as solid's gonna get in radio here (Loop, Drive, Kiss, Mix, WFMT) or is a suburban signal and thus useless.
EDIT: of course, there's WLS-FM; why, it's hardly as if 94.7 hasn't been known to change formats from time to time!
EDIT 2: super-mega-longshot possibility is that they get a permit to put a station at 99.1, which I think is the only open frequency in Chicago. If you count up by .4s starting from 92.3, you'll recognize a lot of those frequencies except for 99.1, which is WMYX out of Milwaukee and seems to be rather strong as far as FM signals go. If I recall, you can get spotty reception in the north burbs. I don't know if the FCC won't let Chicago have a station at that frequency, and I don't know why their signal is so powerful. But maybe that's an option.
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