Why assume these would be Chicago stations? CC has to sell some prime broadcast real estate, despite the soft market created by the current sub-prime capital crunch. Those who can swing the financing may get some deals, and I suspect Oprah gets her calls returned when she calls her bankers.
Besides the 37 small markets in the "Good Radio" deal (which now appears officially dead), Clear Channel had to spin off a number of stations in larger markets because the privatization would result in a significant change in the control of that company. This resulted in a loss of grandfather status in a number of clusters that were assembled under the former contour-overlap rules, but were now over-size under the Arbitron market method of identifying the relevant "market" to set ownership limits. These stations were spun off into the "Aloha Trust."
The "Aloha Trust" has some clusters from fair sized markets--including the Cleveland FM's, and, as I remember, one of the larger Florida markets-Miami?. One story was that these stations would be spun back into the newly privatized CC once the FCC changed ownership rules, (Aloha, of course, means both "goodbye" and "hello"); but it does not appear that there will be any significant changes in the multiple ownership part of the rules. So these larger market stations remain in play.
And then there are the CC television stations--also spun off because privatization kill grandfathered cross-ownership in markets like Cincinnati. Rumor is that the deal for the sale of these stations may fall apart.
Maybe "O" is looking at a few TV stations?