First trip to Chicago
I hate to sound like a foodie, but as a chowhound with some foodie leanings, Charlie Trotters is the best restaurant in America. I have been to many of the restaurants mentioned in the same vein, and I have to say that none compares to Trotter's. If it is within your reach, and you can get a table it should not be missed.
The two meals I have had there, beyond being exquisitely presented with fantastic service, had every component cooked perfectly. So-called "garnishes" were taste sensations unto themselves. I can remember one dish that came garnished with these tiny seared rabbit kidneys that were mind-crushingly delicious.
This is truly the best restaurant I have ever eaten in, and on my list of best meals, they register first AND second.
I visited my sister there last fall and had 2 fantastic meals, from totally different ends of the spectrum.
We had Mexican at Rick Bayless's Frontera Grill. This is a place that I thought really lived up to the hype. Everything we had was fabulous. Each dish had strong, bold flavors, ingredients were fresh, it was just wonderful. I can't remember specifics (possibly because of the first rate margaritas ;-) but go. It's worth it. However, it does involve waiting. We got there about 45 minutes before it opened and were seated pretty quickly. People who came in as we were being seated were being told 2 hours. But, did I mention... it's worth it! Adjacent to Frontera is his upscale restaurant Topolobampo, which might take reservations. And I think Frontera takes reservations for larger parties.
On Milwaukee Ave, we went to a place called Red Apple. Well, the sign is in Polish (Czerwone Jabluszko), and there is a Red Apple on the sign. It's a AYCE polish buffet. Cheap, filling and very tasty. There was a big selection of food and pretty much all of it was good. And it was cheap- I think less than $12 per person.
i had an excellent meal at tizi melloul the last time i was in chi-town. it's a fairly new moroccan restaurant located at 531 north wells street, i think relatively near the theatres. my favorites from the prix-fixe menu (5-courses for $30!): fire-roasted skillet mussels with harissa butter; roasted chicken with fingerling potatoes, artichoke, and tapenade; and while the beef tagine was unremarkable and a bit bland, the saffron couscous that came with it was undoubtedly the highlight of the entire meal.
carson's is _the_ place for barbecue. oh man, those ribs... i salivate just thinking about them.
i definitely recommend getting a hot dog while you're down there as well. and though i'm not a big fan of chicago-style pizza, i know alot of devotees (and most of them seem partial to gino's east).