Shawn...the Alden's are easy to find in Chicago! Look for the Hancock Building (95+ stories tall) and go to the Delaware St entrance. You can't miss Hanig's Footwear!
Here's a nice article on tracking down some Alden's in Chicago:
It would be remiss of me if I didn't mention the Ralph Lauren store just down the way a few blocks on Michigan Ave. Just look for the Mansion next to the Park Hyatt. It's RL's largest store and has a pretty amazing restaurant next to it called...you guessed it RL.
There are Alden's carried by the Brooks Brothers store on N Michigan Ave too.
Good stuff tampatravel. I'll bookmark this site and see how things turn out. If all goes well, I hope to purchase my first pair of in-store Alden's. Thanks a lot for going the extra mile and posting a link in addition the the info you provided.