Bice Ristorante

158 E Ontario St, Chicago, IL 60611 312-664-1474

Description: MAGNIFICENT MILE. Italian management recreates Milan's original Bice at this Michigan Avenue outpost. The stylish place offers sleek Art Deco touches and attentive service. Try an authentic risotto, carpaccio of tuna or swordfish, Milanese veal chop, or a sampler of four delectable pastas. All desserts are made on the premises, and homemade gelato is particularly noteworthy. EL: Red Line to Grand/State
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Caliterra Bar & Grille

633 N St. Clair St, Wyndham Chicago, Chicago, IL 60611 312-274-4444

Description: STREETERVILLE. This hotel eatery's tasty menu adds Californian style to Italian standards. The seasonal menu changes each month, and on Sundays, the kitchen is abuzz preparing for an over-the-top Sunday brunch. Plus, live jazz can be heard in the Calittera Bar. If you're feeling indulgent, dine at the chef's table, which seats 18 amid racks of wine bottles. The full bar serves draft and bottled beers, Scotch, bourbon, and over 100 wine varieties.
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Coco Pazzo

300 W Hubbard St, Chicago, IL 60610 312-836-0900

Description: RIVER NORTH. Perfect for special occasions, this restaurant focuses on hearty Tuscan cuisine. The dining room has a spacious, airy interior, upscale but still comfortable. The food is full of assertive flavors, as evidenced by dishes like pappardelle with rabbit, roast pancetta-rolled pork loin, and herb-crusted half rack of lamb with artichokes and fried polenta. Any of the grilled game dishes is sure to please. The most popular dessert is cioccolato fondente, a chocolate volcano ready to erupt as soon as your fork hits it.
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Gene & Georgetti

500 N Franklin St, Chicago, IL 60610 312-527-3718

Description: RIVER NORTH. An institution and a draw since 1941, this establishment is one of the city's last men's club steak houses. All the waiters are male, and the maitre d' is on a first-name basis with regulars. Moreover, Sinatra dined here whenever he was in the Windy City, indulging in thick, generous steaks and wonderful Italian specialties. These dishes are still around today, thanks to the wonderful tradition that was first started more than 50 years ago. EL: Brown Line to Merchandise Mart
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Giordano's

135 E Lake, Prudential Plaza, Chicago, IL 60606 312-616-1200

Description: DOWNTOWN. No trip to the Windy City is complete without sampling the distinctive deep-dish pizza. A great place to start is the Prudential Plaza location of this popular Chicago-style chain, whose spinach deep-dish has gained legendary status. If meat is your thing, go for the classic cheese pie topped with pepperoni, sausage, and fresh garlic. A variety of pasta and salad dishes is also available. When you head back home, you may get the craving for Giordano's. Don't fret: you can order frozen pizzas via their website! There is another location at 730 N Rush St (312-951-0747).
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Harry Caray's Italian Steakhouse & Bar

33 W Kinzie St, Chicago, IL 60610 312-828-0966

Description: RIVER NORTH. Warm up your vocal cords ­ patrons regularly burst into renditions of "Take Me Out to the Ball Game" in honor of their favorite sportscaster at his namesake restaurant. Plus, tourists often pay homage to the baseball legend by indulging in tasty food that fits the fun atmosphere. Set in a Dutch Renaissance building, Harry Caray's features baseball memorabilia, exposed brick, and cheerful red-checked tablecloths. Classics fill the menu, including pasta marinara, chicken Vesuvio, seafood, and veal. Add in huge, delicious desserts and great service, and you have a lunchtime home run. EL: Brown Line to Merchandise Mart or Red Line to Grand/State
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Il Mulino New York

1150 N Dearborn St, Chicago, IL 60610 312-440-8888

Description: GOLD COAST. Direct from Little Italy in New York City, this latest addition to the Il Mulino family holds fast to traditional Italian offerings and service. Old-school waiters in tuxedos smoothly navigate elegant rooms fitted with mahogany trimwork and Italian marble fireplaces in the 125-year-old Biggs Mansion. They're well-versed in long lists of changing specials and tableside preparation, and they respectfully allow diners to linger over portions so large that they would make any Italian grandmother proud.
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Lou Malnati's Pizzeria - River North

439 N Wells St, Chicago, IL 60610 312-828-9800

Description: RIVER NORTH. This old-school pizza shop knows a thing or two about pies, and locals swear by the place's deep-dish crust, which showcases all manner of toppings. Try the "Lou," named for the restaurant's founder. It includes fresh spinach, mushrooms, sliced tomatoes, and mozzarella, romano, and cheddar cheeses. The "Deluxe" is a great value: cheese sausage, mushrooms, onions, and green peppers. Leaving Chicago? Don't worry ­ pizzas can be shipped overnight to most cities in the US!
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Maggiano's Little Italy

516 N Clark St, Chicago, IL 60610 312-644-7700

Description: RIVER NORTH. For an Italian eatery to stand out in Chicago, you know it must be special. Such is the case with Maggiano's, whose fine Southern Italian cuisine comes to your table family-style or a la carte, guaranteeing that you'll leave at full capacity. J. Cammarrari's Roast Chicken Vesuvio, Picatta-Style Veal Scallopini, and Shrimp Oreganata ­ how to decide? The atmosphere is distinctly Italian, with cozy tables, red-checked tablecloths, and family portraits hanging on every wall.
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Osteria Via Stato

620 N State St, Chicago, IL 60610 312-642-8450

Description: RIVER NORTH. The the golden light cast upon the exposed ceiling beams and stone walls creates a warm, humble atmosphere, not unlike a favorite tavern. Servers suggest the prix fixe Italian dinner, which reinforces the familial atmosphere. Antipasti like fresh mozzarella ciliegine are followed by a pasta (gemelli with sage and brown butteri, for example), leading up to something like braised short ribs with a potato puree and red wine sauce. The restaurant also offers the popular "Just Bring Me Wine" option, where servers take on the onus of selecting the perfect wine for your meal.
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Pane Caldo

72 E Walton, Chicago, IL 60611 312-649-0055

Description: GOLD COAST. At Pane Caldo, it's Northern Italian cuisine served against a backdrop of soft amber-toned walls and a midnight blue ceiling. Tables are adorned with fresh flowers and set with fine china. The seasonal menu changes daily and includes a mix of beef, seafood, and pasta. The risottos are the signature item. Try the fresh Maine lobster or the baked veal shank. Enjoy these delicious entrees to the tune of soft jazz and exceptional service. The international wine list features over 1200 different selections, some available by the glass.
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Pizzeria Due

619 N Wabash Ave, Chicago, IL 60611 312-943-2400

Description: RIVER NORTH. Two true Chicago staples, Uno and Due, serve classic deep-dish pies and are the local shrines that started the Chicago-style phenomenon. Expect a crowd at either of these sibling pizzerias, and be prepared to wait. As you do, dream of a bacon cheeseburger pie, a shroom version, or the signature pizza, loaded with sausage, pepperoni, romano and mozzarella, and loads of veggies and tomato sauce. If, for some reason, you don't crave a pizza, consider burgers, salads, and everything from steaks to seafood and pastas.
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Pizzeria Ora

545 N La Salle St, Chicago, IL 60610 312-464-1872

Description: RIVER NORTH. Deep dish pizzas topped with all manner of goodies have found a niche in this Loop fave, where regulars ask, "How soon until my pizza's ready?" And who wouldn't with toppings such as Canadian bacon, chicken, mushrooms, feta cheese, pesto, pineapple, salsa, and more? Along with pizza, the menu also offers salads, sandwiches, and a host of dinner entrees including shrimp, salmon, and chicken dishes.
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Pizzeria Uno

29 E Ohio, Chicago, IL 60611 312-321-1000

Description: MAGNIFICENT MILE. The place for Chicago-style pizza. Pizzeria Uno, while quintessentially American in theme and cuisine, deserves particular recognition for its fabulous thin-crust and deep-dish pizza pies, which send lunchtime crowds away full and happy. On the go? Check out their fabulous "Priority Lunches," which include everything from Chicken Spinoccoli (baked chicken and broccoli in pesto cream sauce) and classic Chicago pies to fish-and-chips and sirloin tips. If pizza isn't your bag, they also serve tasty sandwiches, burgers, and pastas.
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Rosebud on Rush

720 N Rush St, Chicago, IL 60611 312-266-6444

Description: RIVER NORTH. Basic Italian favorites in traditionally huge portions are what you'll find at this popular restaurant, which includes a breezy outdoor area, the Cocktails and Cabaret room downstairs, and the elegant upstairs room with an azure-blue domed ceiling and large windows looking out over the bustling street. On the menu you'll find great chops, steaks, garlicky rigatoni, veal, and a popular stuffed chicken concoction called Chicken Vesuvio. EL: Red Line to Chicago/State
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Spiaggia

980 N Michigan Ave, One Magnificent Mile, level 2, Chicago, IL 60611 312-280-2750

Description: MAGNIFICENT MILE. For luxurious, upscale Italian dining, Spiaggia is a top pick. One of the town's most romantic dining rooms, it features sparkling platinum-and-white decor, sculpted steel light fixtures, and fantastic Lake Michigan views. The food is simplicity at its best, crafted with the finest aged cheeses, the freshest produce, and wonderful pastas. Delicious dishes include roasted scallops with Parmigiano Reggiano, tenderloin of rabbit, and an unforgettable citrus sea bass. Perfect wines, impeccable service, and irresistible desserts make this restaurant a winner in every category. An 8-course tasting menu is available for $165 per person. A pairing of 8 wines may be added for $90 per person. EL: Red Line to Chicago/State
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The Original Gino's East of Chicago

633 N Wells St, Chicago, IL 60610 312-943-1124

Description: RIVER NORTH. Chicago-style pizza has won droves of ardent fans, and this restaurant is probably the downfall for most of them. Just try to resist the irresistible, deep-dish Chicago pizza with oozing cheese, rich sauce, and fresh toppings from its crisp, cornmeal-infused crust. The spacious dining room seats 500 but still the lines form, and people eagerly await what is considered the best pizza in the town (or maybe anywhere). The ambience is casual with graffiti-covered walls (no profanity!) and dark booths. But people don't come here for the environment; they come for the pizza. You can even take a frozen one home if you call ahead.
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The Palm

323 E Wacker Dr, Swissotel Chicago, Chicago, IL 60601 312-616-1000

Description: DOWNTOWN. Perhaps best known for the caricatures of celebrities that grace its walls, The Palm also serves some of the best steaks in town. The Chicago branch of this New York-based establishment has been enthralling local politicians and sports figures, as well as business guests and out-of-towners, since its 1980 opening. Impeccable service makes dining in this beautiful room all the more enjoyable. Dark woods, rich leathers, hardwood floors, and fine linens blend to create an atmosphere conducive to romance or business.
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Trattoria No. 10

10 N Dearborn St, Chicago, IL 60602 312-984-1718

Description: THE LOOP. Full of business types during the day, this place offers a nice break from sightseeing and shopping in the downtown area. The cavernous underground dining room is peaceful and serene with ceramic tiles, warm colors, and old-style Tuscan charm. Ravioli is the house specialty and is served many ways. Or, try linguine with spinach and eggs topped with prosciutto, roasted shallots, and ricotta and mascarpone cheese. For dessert, splurge on the triple chocolate cannoli. EL: Red or Blue Line to Washington or Dearborn
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Volare

201 E Grand Ave, Chicago, IL 60611 312-410-9900

Description: MAGNIFICENT MILE. If you find yourself in need of a little pampering, try this cozy Italian eatery, where white tablecloths, an open kitchen, crystal chandeliers, and superb service make you feel as if you've just returned home from the war. While most pastas are nothing short of excellent, risotto Volare and osso buco are worth special attention. During warmer months, ask for a sidewalk table.
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