Now this is a thread I could spend all day in.
Chicago Favs:
Cafe Ba Ba Reeba. Part of the Melman Brother's Lettuce Entertain You empire, but oh so good. Spanish Tapas with great social ambiance and almost universally great wait staff. They do know how to train 'em. Bacon wrapped dates, stuffed mushrooms, wonderful sangria... sigh. In a word? Festive.
North Pond To say this is a hidden gem is an understatement on two fronts. Most Chicagoans don't even know this exists and those that do still would have a hard time finding it. There is, to my palate, no finer dining experience in Chicago. You might pay more, but you can't get better. They have a great wine list and make lovely cocktails as well as serving up fresh, locally sourced organic food. Therefore their menu changes frequently. Nummy.
There are plenty of great cheap eats as well.
Hot Dogs:
SuperDawg on Touhy. You may disagree about the "bestness" of the dog, but you cannot deny that they have a great experience. Right down to the packaging.
Gyro:
Andie's. Andie's used to be a hole in the wall drop in joint when I was growing up in the neighborhood. I didn't go for years after I moved out of the area and then finally went for brunch one Sunday. Can't recommend the brunch, but they still have good gyros.
Pizza: Everyone says Duo's, Malnati's or Girodano's. Bullocks.
Pequod's is the place for pie. Just try it.
Sweet Treats: For years I would have said Margie's. Hands down. Margie's is an institution and I think it's a shame that I can no longer recommend them, but after being refused service on my birthday ("we don't serve your kind!!") I just can't support them. Instead I say "
Cupcakes" on Briar in boytown.
Will be back for tips on other places I've lived and visited.