I just spent the last two days eating my way through Chicago and wanted to report back since this site was so helpful in my research. I'm a 'hound from DC and spend much of my time chasing the holy grail of food perfection. Generally, you should consider yourselves very lucky to live in Chicago (with a couple caveats below). Anyway, on to the details:
Sunday lunch - Emilios Tapas on Ohio (downtown). We got in to the hotel around 1 pm, so didn't have much time to look around. This place is a good tip for tourists looking for a place that's open on Sunday for lunch. Decent tapas (eg, grilled country bread with avacado and marinated seafood) and a very nice outdoor seating area.
Sunday dinner - Chilpancingo -- Another good tip for tourists looking for a place that's open downtown on Sunday night. Festive atmosphere, friendly service and terrific food. I had the 5-course tasting menu and my wife ordered off the menu. Highlights were a definitive tortilla soup, corn masa boats filled with chicken/mole, fried plantains and black beans/shitakes, and mahi mahi. When they mistakenly brought a tamale instead of the corn masa boats (you can ask for something specific even if you're doing the tasting menu) they gave it to me for free. So all together I had 6 courses for a very reasonable $49 - and everything was very, very good. I was terribly jealous - we just don't have anything like this in DC.
Monday lunch (early) - Wiener's Circle. A great char-polish and addictive fries. Ate out on the picnic tables. The perfect 'hound experience. Another experience we don't have in DC.
Monday lunch (late) - Stopped for a quick sushi fix at Kamehachi (walking back from the Wiener's Circle worked up my appetite). Good, fresh sushi, totally unplanned stop.
Monday late afternoon snack -- Garrett's caramel corn. Simply the best caramel corn I've had - and I've had a lot.
Monday dinner -- Tru. 7:30 pm reservation, didn't leave until after 11:30 pm. I feel somewhat torn about the experience. My wife got the seafood collection ($135). I started with the tomato tasting menu ($110)but switched to the regular chef's tasting menu ($135)after the first two course were just okay (heirloom tomatoes in bento box and peeky toe crab with green zebra striped tomato). Plus they couldn't get the temperature right and there were streams of cold air blowing across the room (it was so cold that all the shawls were snapped up by various women around the room). My final complaint is that the wait staff seems awfully young to be so pretentious - and many of them seem to go to the same barber and have spiked hair with a lot of gel). Having said that, things picked up considerably when I moved to the chef's collection. The foie gras was perfectly cooked - crisp on the outside and melting on the inside. The lobster bisque was terrific, and the beef short ribs are unbelievably good - so tender, completely void of fat, they say it's a 24-hour preparation and I believe them. My wife had some hits (tender steamed scallops, poached tuna in a delicious Japanese broth, roasted loster) and some misses (boring Alaskan char). The biggest surprise was dessert. I was all geared up for Gale Gand's magic, but they were all disappointing. I had a black cherry bread pudding that was muddy and a rhubarb pot pie that was fine but nothing special. My wife had a couple of chocolate things, including a molten chocolate cake, that have been done to death. The root beer float was cute but no great shakes (no pun intended). They did give us a complimentary after-dinner brandy to make up for the earlier chill (which was fixed about halfway through the meal). Then we got a tour of the kitchen, as suggested by someone on this board. Very cool. Chef Tramonto was incredibly organized - there were labels on everything, including the tomatoes. That's sort of how I feel about the place - highly organized, technically proficient, but perhaps takes itself too seriously and lacks a certain passion. Incidentally, I should mention that neither Chef Tramonto nor Gale Gand were there that evening. Don't know if their presence would have made a difference.
All in all, though, a fabulous eating adventure in the Windy City. Thanks for all your help. I'll be mail-ordering Garrett's (although it won't be warm) and would love to open a Wiener's Circle or Chilpancingo franchise in DC.