The latest word with perennial hometown hero Vince Vaughn is that his ludicrously expensive triplex penthouse at The Palmolive keeps shedding millions. It's presently at $18.4M, down from $24.7M. So, we suppose you could say you're getting a deal. If that's how your mind works. Vaughn also has a River North townhouse that, at last check, was available to rent for $9,500/mo. It's never scored more than $7,000/mo.

We figured a major adjustment was just around the bend for MJ's 56,000-square-foot Highland Park estate. Listing 18 months ago for $29M, the seven-acre property took a $8M price chop early in the new year. There's probably nothing quite so over-the-top in all Chicagoland. The 9-bed home comes with seven gated acres, garage parking for 15 cars, pool, pond, tennis court, and putting green. How much for a night?

The sprawling Lake Forest home of late filmmaker John Hughes re-listed in January with an $885K price chop. That brings the ask to a shade under $5M, almost reasonable for 11,000 square feet of living space on two lake-proximate acres. And guess what? It's still on the market.

18-year NBA vet Juwan Howard might be finishing his career in Miami, but he's a Chicagoan at heart. He made the Celebrity Real Estate roster for the early-year listing of his 53rd floor Trump unit. Asking $2.9M, the place has some of the building's jazziest decor including a map print wall, glass wine room, and Brazilian hardwood floors.

With a freshly minted and very lucrative contract extension, Bears' running back Matt Forte has done the sensible thing and put his Vernon Hills McMansion on the market. Join us in the city, Matt. The living's real good.

Former Bulls and Clippers head coach Vinny Del Negro, forever on a short leash, sold his Highland Park contempo for $1.2M in February. The new owner immediately re-listed the property, which sold once more in August for just $700K... not that we can fault a game of hot potato with such an ugly home.

Longtime Fox local news anchor Robin Robinson sold her 5-bed Bucktown digs in early September for $1.175M. She originally listed the newish home in May for $1.29M, with pending empty-nester status as one possible motivator.

Ex-Bulls power forward, 19-year NBA vet, and current celebrity golfer Charles Oakley took a modest loss on his Museum Campus-proximate South Loop condo back in June. The 10th floor 3/3 corner unit fetched $900K, whereas Oakley paid $950K in 2005.

Electric Blackhawks captain Jonathan Toews, an integral piece to the Hawks' two Stanley Cup victories in the past five years, sold his shimmering sky-high Lakeshore East condo with floor-to-ceiling windows in August for $1.629M-- just $71K off the asking price. Not to fear, Toews is still in uniform and still in possession of another nearby condo.

Fall Out Boy guitarist Joe Trohman put his blinged-out rock-and-roll townhouse on the market in August in the Southport Corridor. The 2,000-square-foot home, of MTV's "Cribs" pedigree, is asking $849K and is open this Sunday for a walk-through.

24-year vet of ABC-7 newscasts, Sylvia Perez, lost her contract this year and has now listed her crazy Hinsdale spread for $2.4M. The opulent "private paradise" has a masterful pool, waterfall, and grotto and may well sell for less than the $2.2M Perez paid for it in 2006.

David and Susan Axelrod sold their incredible 46th-floor Lake Point tower condo above ask for $1.28M. The political advisor-turned-academic is settling in to a new leadership gig at U of C, and chose his Water Tower Place condo over this one (damn, that must be a fine place!). The buyer gets 3,200-square-feet of living space with lake, city, and Navy Pier views.

Founding member of the Smashing Pumpkins, guitarist James Iha, left his Egdewater single-fam several years ago for NYC opportunities. He finally got around to selling it in late August, for $545K. Iha had listed the comfy 1910 American Foursquare in June for $625K.

Recently-traded Cubbie Alfonso Soriano (to the Yankees) listed his penthouse at The Pinnacle in September for $2.95M. It's a pretty sweet place if you're a fan of perilously high terraces and marble finishes. The staging might be stiff, but lord it's hard to argue with a 3,800-square-foot condo in the clouds.

R. Kelly's repossessed Olympia Fields mega mansion and estate has a private buyer under contract for roughly $587,000. Chase bank seized the property at auction in the Spring for a paltry $950,000 and procured the buyer. The 14,500-square-foot mansion and three-acre grounds could have and should have yielded something closer to $5M in healthier circumstances.