It’s hard to pinpoint exactly when Emmis Communications decided to give up on Chicago. But in a report released last Friday, the company left no doubt that it’s ready to throw in the towel on its two stations here.

In its annual filing with the Securities and Exchange Commission, the Indianapolis-based owner of classic rock WLUP-FM (97.9) and alternative rock WKQX-FM (101.1) set the stage for the sale of both Chicago stations (as well as one in New York, believed to be the underperforming WRXP-FM), stating:

“We also regularly review our portfolio of assets and may opportunistically dispose of assets when we believe it is appropriate to do so. In particular, we have one radio station in New York City and two radio stations in Chicago where we believe the sale value could exceed the prospects for cash flow generation as part of our portfolio. Although we remain optimistic about the growth potential of these stations, as the market for buying and selling radio stations improves, we may from time to time explore sales of one or more of these stations.”

Tom Taylor, executive news editor of Radio-Info.com, discovered the telltale passage in the 99-page filing and deduced which of the company’s four New York stations could be on the block. But the wording left no question that both the Loop and Q101 also have giant “for sale” signs on them. “If [Emmis CEO] Jeff Smulyan is listening to offers, at least one of them may be about going sports,” Taylor wrote in his newsletter Monday. “There have long been rumors about Jeff himself going sports in Chicago.”

Sports is not the only scenario Smulyan may be considering. Others who’ve approached him say they found him ready and willing to unload the Chicago properties on anyone who comes up with the right price. The trouble is, under Emmis’ stewardship, they’re worth a lot less than they were before.

As I pointed out here after Emmis dropped iconic morning star Jonathon Brandmeier, the Loop hasn’t been a real Chicago radio station since it fired some of its smartest people last spring and outsourced all programming, imaging and branding functions to St. Louis. With the recent departure of afternoon personality Eddie Webb, the Loop lost the last real marquee name from its lineup. What once arguably was the premier rock radio brand in America is now the station of Pete McMurray and the‚ “Loop Rock Girl.”

In many ways, Q101 is hardly better off than the Loop. The station that once handed out $20,000 in iPods to top media buyers and advertisers (in a disastrous promotional campaign that only called attention to its looming competition) can offer little more today than listeners can get on their own digital devices — one exception being the morning duo of Brian Sherman and Steve Tingle, who troll each month for a “Token Hottie.” Starting to see a pattern here?

Four years after Mancow Muller was fired as morning personality — causing Q101’s revenues to plunge — his multimillion-dollar lawsuit against Emmis still haunts the company. Another legacy of the Mancow era was the $300,000 payment Emmis made to settle its record of indecency complaints with the FCC. But the 2004 consent decree only covered complaints that had been lodged up to that point. Are there additional time bombs set to go off? Here’s another nugget contained in the filing last Friday with the SEC:

“Subsequent to the approval of the consent decree, the company has received letters of inquiry from the FCC alleging additional violations of indecency rules. The broadcasts covered by these letters of inquiry are not covered by the consent decree and could result in the imposition of liability.”

I say good riddance to Emmis for squandering not one but two historic radio franchises in Chicago. But here’s hoping whoever tries to buy them is smart enough to read the fine print.