Didn't get much traction but I am hopeful about the prospect of these 2 Illinois Center buildings possibly getting a more interested owner.
http://chicago.curbed.com/archives/2...s-for-sale.php
That Wacker frontage just next door could be crucial in drawing tourists and traffic on wacker east of Michigan. Right now, when you cross the dusable bridge going south you either go straight to head toward the park and to see if mag mile keeps going (it doesn't) or you turn right to follow the river or head toward the loop. You definitely don't turn left, because all that's up that way is the tacky marble front of an Art Deco building with a tacky looking Fannie May store, then the rest is an uphill barren stretch of plaza and motor courts and zero people. Oh, and a Houlihan's with no frontage. This is where Wanda wants to plop its billion dollar supertall.
As for the other tower, Michigan south of Wacker is undergoing a blitz of revitalization, tons of new high-profile retail is on its way and it wants desperately to pull mag mile tourists south to continue spilling money out of their pockets by creating a whole new sidewalk-level continuity of shiny new stuff to keep pulling people in. There's a bit of a gap on the east side, though, between 333 N Michigan's ongoing new retail buildout (which is almost leased up I believe) and the stuff south of Water street, like Sweetwater restaurant, some light retail, and then the huge new retail buildout at Millennium Park Plaza which is also filling fast. That boring gap kills the continuity a bit for half a block or so. The 2nd Illinois Center building up for sale happens to own a piece of that gap, and even has air rights to build over upper Water street.
Both stretches of road (Wacker going east, Michigan going south) have vital weak spots in their streetfront integration, and right now you can 2 buy buildings and fix those weak spots with some smart retail-focused reconfigurations. You'll just need $425 million to do it.
As a bonus, the buildings you'd have bought would happen to also have been designed by a beloved and world-renowned architect and Chicago legend.