i'm jealous....chicago's my home town and i miss it. haven't been there since september. i miss italian beef sandwiches (or combos), deep-dish pizza, good mexican food. did you know they don't use cilantro in italy?
best pizza--uno's and due's are great landmarks if you haven't been. and the pizza is still the best in town. you must get it with sausage and experience the "manhole cover" sized patty they put on it. for thin crust pat's pizza on sheffield is really good.
best bar--empty bottle for live music
best coffee--my friend jason has a coffeehouse in logan square...kind of off the beaten path, but a really nice area to check out. lula cafe at kedzie and logan blvd. near the logan square el stop on the blue line. they've got great coffee, a great funky atmosphere, multi-cultural food, lots of vegetarian dishes, and it's just one of those places where you can hang out a while, read the paper. go say hi for me.
a good market to check out is the south water market near the university of illinois at chicago. south and west of the loop. this is a great old historic market area that is destined to be torn down very soon. tons of produce...this is where most grocery stores in the chicago area buy their fruits and vegetables. a great purveyor there is cornille and sons. they supply all the finest restaurants like trotters, ritz, seasons, etc... tom cornille is a very friendly guy and i'm sure he wouldn't mind talking to you.
you could also go to maxwell street market if you're around on a saturday morning. this is also near the university and for years it was an impromptu flea market bustling with old bluesmen and bootleg porno vendors. since the u of ill. bought the land it was on, the city moved it a few blocks away and gave it an official site and now its a little cleaned up, but still great. you can eat the BEST mexican food there. just about every stand is cranking out fresh masa tortillas and serving them faster than they can make them. rick bayless did an article about it a couple years ago for saveur.
i'd also urge you to eat a maxwell street polish while you're down there, with mustard and grilled onions. also a beef sandwich from al's beef on taylor or mr. beef on orleans is required for a full chicago culinary tour.
more great food: mirai sushi on division is doing cutting-edge sushi of the highest quality. wishbone on lincoln still has really great downhome southern-style cookin' even though they moved from their cool small original location to this huge shiny new space. the food's still the same and you still get hot corn muffins on the table.
can i live vicariously through you? let me know how you liked it all...