4 places for different price ranges:
$$$$ Alinea
Really expensive, but the best food in Chicago for a foodie. Lincoln Park. Price per person around $150 to $200. It is a 24 course, small plate food extravaganza.
www.alinearestaurant.com
$$$ Boka
Still expensive but not too out there. These guys are in the restaurant reviews every week. Lincoln Park. Price per person around $40 to$80, depends on how many courses and if you have drinks or wine.
www.bokachicago.com
$$ Uncommon Grounds
They do all of the things that really high end restaurants do. Microseasonal rotation of the menu, organic, veggie options, decent wine list, great food, two locations. $20 to $40 per person, also depends on courses and drinks.
http://www.uncommonground.com/
$ Sultan's Market
It's like Mediterranean fast food! Get a rockin' falafel for like $3.50, side dishes, awesome lentil soup, great salad bar, cool location. (Wicker Park, not Lincoln Park). My favorite restaurant in all of Chicago, mostly due to the economics of it. $5 to $10 per person, no alcohol.
chicagofalafel.com/
Tru, which after many years of fooding, is still the best meal I've ever had. A 3-4 hour degestation of fabulous dishes (the lobster capuccino and the caviar tower are legendary) that will blow your foodie-friend's mind. I will say that all of the other places mentioned in most of the other answers are excellent choices too (although Rock Bottom and Cheesecake factory are pretty run of the mill) but for me Tru still shines. Here are a couple of other thoughts:
Your friend has to try a proper Chicago hot dog. I think Weiner Circle in Wrigleyville is the best, but make sure wherever you take him has the proper fixings--a Vienna dog, A poppyseed bun (preferably from Rosen's) sport peppers and electric green relish, in addition to the other ingredients that make a real Chicago dog. (tomato, pickle spear, celery salt, onions, mustard.)
For an Italian Beef, you should try Johnny's on the West side in Elmwood Park, or Portillo's.
You should really try two different types of Chicago pizza, stuffed and deep dish. Giordano's or Nancy's for the stuffed, Lou's or Gino's for the deep dish. Even better, for deep dish try My Pi on Clark near Diversey, my choice for the best. Please don't get caught in the touristy trap of sending him to Uno's or Due's. (I'm not gonna start that whole argument again but please don't bother with Uno's.)
A gyro would be nice and for some reason Chicago always seemed to make them better than any other city I've lived in. You can get a really good one at Hella's Gyros in Uptown.
Finally, ribs. Lots of very good choices and the only MUST on the list of great BBQ in Chicago is the original Leon's on the south side. Don't go to the newer north side location, it's a cheap, bland, safe whitey version of the original. Give your friend a good Chicago neighborhood experience and take him to the best, Leon's. Really, though, most BBQ places in the city are excellent.What's the best restaurant in Chicago to take a foodie?
Avec (Chef Paul Kahan)
Blackbird (Chef Paul Kahan)
Publican (Chef Paul Kahan)
Frontera (Chef Rick Bayless)
Xoco (Chef Rick Bayless)
Topolobampo (Chef Rick Bayless)
Alinea (Chef Grant Achatz)
Moto (Chef Cantu)
L20 (Chef Laurent Gras)
Great Lake (rated as the best pizza in America)
...or try an underground dinner event. http://www.xmarxchicago.com/ You have to sign up for their e-mail newsletter to find out about the events and the events sell out really fast when they are announced.
I went to one of their dinners a few weeks ago and it was amazing food and really fun and interesting!
The Purple Pig on Michigan Ave. is brand new and getting a lot of hype. Bacon makes everything better.
If yu are looking for restaurants named after a person in sports take them to either Harry Caray's or Mike Dikia's restaurant. Or you can look around http://chicago.metromix.com/ for ideas, and see what people thoughts of different restaurants in Chicago. Here are the lunch and dinner menus for Harry Caray's, http://www.harrycarays.com/menus_chicago鈥?/a> . And here is the lunch menu for the Chicago location of Mike Dikia's http://www.mikeditkaschicago.com/downloa鈥?/a> , and here is their dinner menu , http://www.mikeditkaschicago.com/downloa鈥?/a> . And Harry Caray's also has locations in other places in Chicago area, including soon coming to Navy Per. And Mike Diki's also has a location at Oak Brook Terrance. Normally if I dine in Chicago, it will be pretty much at a pizza place, and there are also sorts of Chicago style pizza restaurants that you might want to take your friend to. And in the summer time, if your friends hasn't been to all sorts of restaurants by then, take him/her to Taste of Chicago, so they can even try food from the restaurants even more then one in a day. There are also restaurants on Navy Pier that you friend might like to go, including Bubba Gumps, that is if you can get into the restaurant. You can find out what restaurants are on Navy Pier at http://www.navypier.com/din_shop/dining.鈥?/a> . Harry Caray's Tavern is coming to Navy Pier, and that opens on March 1st, 2010. If you don't want to dine at a sit down restuarant on Navy Pier, there here are their food court places http://www.navypier.com/din_shop/dining_鈥?/a>What's the best restaurant in Chicago to take a foodie?
Cheesecake Factory
Gino's East
Rock Bottom
It depends on what they like to eat.
http://chowhound.chow.com/boards
http://www.chicagofoodplanet.com/
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