I've been in Chicago for the last couple weeks working a large project.
Gotta say - I love this town!
Almost everyone I've met here has been really friendly and pleasant to interact with - there was one cabbie that irked me so much that I wadded up a $10 and threw it at his head - but outside of that it's been a great experience.

"The Source of the Trouble" arranged a couple of condos for the month for me and the guys which has been pretty awesome.  Staying in a hotel for a month stinks, even when it's a nice one.
Renting a condo lets have a bit more space and you blend in with the locals a little more.

Places we like:

http://www.thefrontierchicago.com/
Whole smoked alligator.  For Reelz.

http://doritedonuts.com/
I know I've gained 5 pounds eating these little bits of heavenly cakes.

http://www.delilahschicago.com/
Great dive bar.

http://stocksandblondesbar.com/
Ditto.  And right under the stairs to the L.

http://www.chicagobluesbar.com/
Love this joint.  Like Northside Tavern in Atlanta.

http://www.hugosfrogbar.com/
A little more upscale than I normally go for but the bartender was entertaining as hell.

http://bavetteschicago.com/
The guys and I had 2 fantastic meals here.  Order the bone marrow.  Seriously.  Incredible.

http://www.thefryecompany.com/frye-flagship-stores/
The Frye Company Chicago Flagship store on North Rush Street.

http://shop.nordstrom.com/st/nordstrom-michigan-avenue
Turns out that the high price you pay at a store like this is worth it when you also get excellent service and a friendly, helpful staff that will find just what you need.

The Parsons Chicken & Fish El Camino.

http://www.parsonschickenandfish.com/
Excellent fried chicken and butter-beans - north of the Mason/Dixon line!!

http://www.speakeasycustomtattoo.com/
I met the owner, Patrick, and talked to him about getting another piece.  Nice guy and amazing artist.  The shop itself is gorgeous too.

If you come to Chicago, the area around Wicker Park is pretty amazing.  Wander around; you'll find something.