As an out-of-towner, I may as well pipe up since I'm on the boards. First, you might as well see some of my previous adventures:
http://www.extramsg.com/modules.php?que ... ame=Search
http://www.extramsg.com/modules.php?nam ... cle&sid=18
http://lthforum.com/bb/viewtopic.php?p=128029#128029
Notes from One Night Through Town:
* Al's Italian Beef: regular Italian beef very moist, falling apart thinly sliced beef; dipped in super flavorful meaty, garlicky juices; spicy peppery side with slight vinegar flavor and crunchy, spicy, tangy celery; sausage is dense and perhaps too chewy but meaty and spicy; dipped as well;
* Aroy Thai:
- sour sausage is sweet with tangy finish sausauge; porky with rice that keeps it moist;
- northern sausage is somewhat dry, but not too bad; lemongrass and red curry flavor; a lot of herb, somewhat grainy
- bamboo shoot salad has pickled bamboo shoots that have a fresher flavor, tangy and interesting, than what I'm used to, almost aromatic/fragrant; balanced very well in teh salad
- waterfall beef is very tender, caramelly, and moist; very spicey, but undertone of sweetness; nice toasted rice texture on outside
- green papaya salad came with salty crab and nice chopped papaya with lots of fishiness;
- soup has strong sweetness and lots of fragrance from anise and lemongrass and kaffir lime; good tangy finish; beef juicy and thick; straw mushrooms; intensely flavored
- larb has a really earthy flavor almost like a Mexican picadillo, perhaps cuminy or cinnamony with chile flavor; has lots of offal, such as tripe, kidneys, and liver and then toasted rice;
- stir-fried chinese broccoli are cooked perfectly, not overcooked; strong fishiness with some minced pork and spicy chiles; nice fishy aftertaste
- bamboo shoots with pork; same fragrant bamboo shoots as dish from before; very well balanced
- pat ped has pefectly cooked thai eggplant; green beans perhaps a little undercooked; decent but not one of my favorites; perhaps a little bland;
Here are the things I wouldn't miss:
* Al's Italian Beef: Get it dipped
* Mario's Italian Ice (definitely lemon)
* Deep Dish: I've liked Malnati's butter crust with sausage and Giordano's stuffed with spinach
* Hot dog with all the Chicago fixings: relish, pickle, celery salt, tomato, etc.
* Garret's Popcorn: Get the mix, but only when it's fresh.
* BBQ at Honey 1
* a jibarito
These are some of the things I've felt were uniquely Chicago and also very good. I agree with the rec for TAC Quick. I've had two excellent meals there. You can get some great food with dishes you won't find anywhere in the US except a few select places or in LA at some other Thai restaurants if you stick to Erik M's recs. Since you're from New York, I'd also recommend getting some regional Mexican while you're here.
If you're in the loop and looking for a tasty bite, my wife and I really liked Bombon for Mexican influenced sandwiches.