Just came back from spending a great week in Chicago (business trip - but got lots of pleasure out of it).
Went to a great restaurant called the Mashed Potato Club. You can get regular food also, but their specialty is mashed potatos. Basically, you can choose whether you want a 1, 2, 3, or 6 scoop dinner. You can also choose to have one of the mashed potatos be sweet potatoes (yum, topped with brown sugar). Then, you get to pick your toppings, from cheese to meats, to all sorts of vegetables. I got 3 scoops, 1 plain, 1 with goat cheese, and then the sweet potatoes. It has a very eclectic atmosphere - and apparantly on Monday night they've got a great drag queen show.
They also have build your own sundaes and toppings for dessert. The marshmallows were great, since they were mini and toasted (my favorite).
Other places I enjoyed:
Eli's - for their steak, cheesecake, and liver pate (which really surprised me). It tried the liver & onions appetizer, which they're famous for, but I didn't care for it. I also headed out to the factory - they have imperfect cheesecakes (like no whipped cream, or some other tiny detail) for almost 50% off. I came home with lots of great desserts. They also made a cheesecake milkshake - made from a whole peice of cheesecake! I got the white chocolate raspberry shake. If only you could have seen my smile.
Other places I visited:
Navy Pier - got a great chocolate and toffee covered waffle from a little fudge shop.
Corner Bakery - great chicken salad, made with currants.
Chicago Flat Sammies (across from the water tower) - great sandwhiches and homemade chips.
Indian town - there was a great place that had the best egg rolls, made with peanut butter, and stopped at a Sweets place for some Jalebi (kind of like a honey funnel cake).
Margie's - for great ice cream sundaes
Some hot dog place where they have big plastic hotdogs on top of the building (guy and girl) and they wink at each other - great onion chips and good dogs.
I know I'm missing a few, but I really had some good eats. Can't wait to go back.