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Chicago Diary #2: What You REALLY Wanted to Know About Chicago: FOOD

March 10, 2009
by Mark Hagland
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When I happily agreed to write a series of blogs about Chicago, directed towards HIMSS 2009 attendees in the month preceding the annual conference, my mind immediately went to the soaring architecture of my beloved adopted city, to its tremendous cultural life of symphony, opera, jazz, museums and art galleries, to its incredible history, and its great sports venues and outdoor spaces, and its colorful neighborhoods and rich history.

Yeah, yeah, nice, said my colleagues at HCI. Now tell us about the food!!! And, of course. Who wouldn’t want to know about Chicago’s dining options? This is a great eating city, with a range of restaurants ranging from the five-star down to the most amazing little storefront ethnic eateries, representing just about every cuisine in the world. Of course, therein lies a challenge: every issue of Time Out Chicago, every issue of Chicago magazine, and countless listings in the city’s two major newspapers, the Chicago Tribune and Chicago Sun-Times, as well as endless online and other venues, all provide regular restaurant listings for the hungry and the curious. But below, please find a thumbnail guide to a few famous first-class restaurants, several nice mid-range choices, and a bunch of cozy favorites of mine—all within a 15-minute taxi ride from downtown.

So, don’t worry—you won’t starve when you come to Chicago for HIMSS! And, here goes…

Group 1: Fancy-pants haute cuisine

Charlie Trotter’s Chicago ( 816 West Armitage, Chicago 60614 / (773) 248-6228. This is the ne plus ultra of Chicago restaurants; it’s won so many awards, they can hardly keep track. Among them, Wine Spectator called this “The Best Restaurant in the World for Wine & Food” (1998) and “America’s Best Restaurant” (2000). Owner Charlie Trotter keeps his patrons awed at this palace of nouvelle cuisine regionale, with its various tasting menus and dramatic presentation. Unfortunately, you may just have to take out a second mortgage to afford to eat here (I still remember my one Trotter’s experience nearly 15 years ago—dinner for six ran to over $1,400 including tip!). Seriously, don’t expect to spend less than at least $200 per person here at a minimum, not including wine or dessert (and the wines here are all top-end). In any case, if the prices don’t put you off, you’d better reserve now if you want to get in at HIMSS-time—tables, especially in the pride-of-place kitchen, are frequently booked several months in advance.

Spiaggia (

980 North Michigan Avenue, Chicago60611

/ (312) 280-2750. Nothing can beat Spiaggia for its great view (overlooking OakStreetBeach, thus the restaurant’s name, which means “beach” in Italian) or sense of occasion. This upscale Italian eatery is fancy (yep, there’s a dress code) and urbanely elegant. I haven’t been to Spiaggia in several years, but I’d expect to pay close to $100 per person for dinner—a bargain compared to the prices at Trotter’s, above). But dining here is always enjoyable and tasty, with its fancy versions of well-known Italian dishes. You can have most of the same dishes next door at Café Spiaggia for probably about half the price, and you don’t have to wear a jacket and tie next door, either. A fun experience.

Tru (

6767 N. St. Clair St., Chicago

/ (312) 202-0001.
Tru lies somewhere between Charlie Trotter’s and Spiaggia in terms of cost, meaning you won’t have to take out a second mortgage on your house to eat there, but don’t expect to get out of this place without shelling out at a very minimum $100, not including wine or dessert, probably somewhat more. This high-end, high-attitude eatery offers “progressive French cuisine at its finest,” as its website proclaims. Just don’t expect to leave fully sated—this is a true “nouvelle” restaurant. Add bonus: it’s a good place to see and be seen, if you’re into that. Chic people, chic food, chic décor.

Group 2: classic American cuisine

RL Restaurant (

115 E. Chicago Ave., Chicago60611

/ (312) 475-1100. This young-ish restaurant, located inside the Ralph Lauren area flagship store at

Chicago Avenue


Michigan Avenue

, focuses on American classics, including crab Louie, steak Diane, and green goddess salad. It’s somewhat pricey for what you get, but its location will be extremely convenient to those staying in

North Michigan Avenue

hotels. Hey, want a side of khakis with that…??

Custom House (

500 S. Dearborn St.

at Congress Prkwy (312) 523-0200. This highly regarded steak house is located very conveniently for those staying in the South Loop area. Standard American dishes, with a regional and seasonal focus, are done well here, and the price of a three-course prix-fie lunch is only $24.75 (dinner is somewhat more).




You're welcome, Daphne! Enjoy the degustation...!

Mark, Have you ever been to Farmerie 58 on E Ontario?

Thanks, Tim Tolan and Neal Ganguly! And, you're very welcome, Tim! Neal, have not yet been to Farmerie 58, but I bet there are reviews available of it online... it's definitely in the "chic" part of town, though, that I can say for sure... :-)

I think you may want to include a few notes to your post, which by the way, is excellent!

First, for the high-rollers, why not have a cocktail or after dinner drink at 95 in the Hancock Center? On a clear night, you can see all the way to the light reflecting from Milwaukee. Great view, never eat there.

For the mid-range folks, visit the original Morton's. Still great steaks and the Bears and Cubs players regularly hang out there.

On a budget? How about Chicago pizza? Geno's is as good as ever, or attendees could visit the original Uno. What a shock, what with the décor . . . or lack there of.

And for a Chicago Vienna hot dog or Italian Beef sandwich all under one roof, there's Portillo's on Ontario. Not the very best of each, but still good enough to warm the coldest of hearts. Hint: order an Italian Beef Combo, the sausage in Chicago is unmatched, and add a few peppers!

By the way, did you know that O'Hare has been rated numerous times as having the "second best" hot dogs in the U.S., mostly next to Miller Part in Milwaukee (because of the unique mustard)?

My two cents. I lived in Chicago for 21 years, and love it and its peaple dearly. If it weren't for the damn winters, I'd still live there. But Global Warming gives hope. Go Cubs, great post! Thanks,


Mark, any recommendations for local dive serving amazing, non-fancy food for locals a la Calvin Trillin?

Sweet post Mark. I have pasted into my Blackberry for the trip to the windy city. Thanks for the list!

Thanks Mark! Anybody need a date for Trotters? (Just kidding, OF COURSE)