If one uses an Income Approach method of valuation based on Cumulus' mediocre cash flow from these two stations, the conclusion of value would likely be far under $50 million. However, I contend a better operator (read: Hubbard) would be able to extract more cash flow.
Precedent transactions should be considered when trying to arrive at an estimate of fair value. One that quickly comes to mind - at least for me - is the recently closed sale of the former KSWD-FM in Los Angeles to Educational Media Foundation. EMF buys stations based on "stick value," not cash flow generation ability of an existing format. In that case, I believe EMF paid about $50 million. Granted, Chicagoland's economy isn't as wealthy and the region isn't as highly populated as the greater Los Angeles area, but if a station such as KSWD can fetch a stick value of around $50 million, I think a Class B stick in Chicago is worth maybe 40% to 50% that figure. (Bear in mind 100.3 MHz in L.A. is a grandfathered Class B with a power/HAAT combination closer to a Class C1 or Class C0 station.)
I think the "right" number probably isn't terribly far from the $50 million amount Merlin had been seeking. I would say a range of $42 million to $45 million. A good operator should be able to grow these stations to $8 million a year in annual EBITDA (combined) within a couple years of acquisition.