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To visit our next Icon, we’ll make a right on Sunset and motor east toward the Windy City…
As Travel & Leisure wrote recently, “There’s just no stopping Chicago on its march toward the title of America’s Dining Capital.” So while exciting new choices like L20, Perennial and Urbanbelly abound, let’s visit three old standbys first.
Gibsons Bar & Steakhouse
1028 North Rush Street, Chicago, IL 60611 (312) 266-8999
At the very center of Chicago’s Gold Coast, smack in the middle of raucous, rollicking, Rush Street, sits the very essence of the Chicago nightlife, bar and restaurant scene, Gibsons Steakhouse. Ghosts of legends past haunt the place, which was once Mr. Kelly’s, one of the premier jazz clubs in the country and home to many great live jazz albums by Sarah Vaughn, Ella Fitzgerald, Anita O’Day, and many others.
 
Gibsons is renowned as one of the great American steakhouses, and in good Midwestern fashion, for its enormous portions. Begin with a drink at the big curved, mahogany bar, in the helpful hands of very experienced barmen who treat everyone like a regular. The overhead TV is tuned to the game, while the piano player sings and swings the standards. Celebrities stand toe to toe with the rest of us mortals enjoying the scene.
 
The dining rooms have a slightly calmer feel, with their sleek Art Deco decor and bow-tied waiters. Huge cuts of meat are brought in on trays for your selection. The twice-baked potatoes are great. There are plenty of fish options including planked whitefish and massive Australian lobster tails. One dessert will feed a table of four. Reservations aren't required, but if you don’t have one, be prepared for an hour wait, which given the bar scene, is not all bad.
Gene & Georgetti
500 North Franklin Street, Chicago, IL 60610 (312) 527-3718
A snapshot of old Chicago, Gene & Georgetti is a family-run restaurant that's been serving up steak and Italian classics in a wood-frame house, in the shadow of the El, since 1941. This “40’s” time capsule was founded by Gene Michelotti and his partner Alfredo Federighi, who was nicknamed “Georgetti” after a famous Italian cyclist. Located in the heart of River North, Gene & Georgetti is Chicago’s oldest and one of its finest steakhouses.
 
The restaurant is dark and clubby, and the (exclusively male) waiters seem to have worked here for decades. The wood-paneled downstairs dining room is often reserved for regulars, politicians, and visiting celebs, although if you make a reservation on the early side and dress well, there’s a chance you might avoid being banished upstairs. (A small gratuity to the maitre d’ won’t hurt but don’t quote me.)
 
It’s where “the elite meet to eat” and legends like Frank Sinatra, Bob Hope, & Lucille Ball as well as modern day celebrities like Russell Crowe, Vince Vaughn, and Will Ferrell, have helped make Gene & Georgetti a classic old-time Chicago place to dine.
 
For my part, I have never had a steak here that was not cooked exactly as ordered. There is also a great seafood fra diavolo, linguine with mussels, clams, calamari and scallops in a spicy tomato sauce. For side dishes, the house salad is refreshing; chopped iceberg lettuce with a buttery texture and wedge of ripe tomato with house dressing, a light vinaigrette. Don’t forget the cottage fries.
 
The wine list is not that interesting but I did find a good Rosso de Montalcino that won’t have you looking for TARP money.
La Scarola
721 West Grand, Chicago, IL 60610 (312) 243-1740
Chicago is a Mecca for outstanding Italian dining, with more than its fair share of solid family restaurants serving traditional southern Italian cuisine. With unpretentious atmosphere and service, La Scarola is a local favorite for good Italian food at reasonable prices. To quote Zagat’s: “You feel like Grandma is going to walk out of the kitchen and pinch your cheeks.”
 
The restaurant has an open kitchen, just a few tables and a restored fireplace against the east wall. Seating is tight, but the room is warm and mellow enough that conversations and clanging pots and pans don't drown out the Sinatra, Billie Holiday and Louis Prima being played on the house sound system.
 
La Scarola has the pedigree of one of Chicago's best restaurant families, the Mondellis, whose much-loved Kelly Mondelli's, was a fixture on North Clark Street for years. Many of the Mondelli favorites are back at La Scarola, including the eggplant parmigiana, the veal and sensational sausage and peppers.
 
Consistently one of the best medium-range Italian tratorria’s around, this packed River West’r features excellent, no-nonsense comfort food, with huge bowls of fresh pastas and a reasonable Italian and American wine list.
 
Appetizers include bruschetta drenched in olive oil, spicy shrimp Armani, and asparagus salad with goat cheese. For dessert, try Italian ice, cannoli with chocolate chips or Italian cheesecake.

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