Bandera

535 N Michigan Ave, Chicago, IL 60611 312-644-3524

Description: MAGNIFICENT MILE. Expect a crowd at this lunch hotspot. Bandera serves superb American fare, and the selection of entrees ranges from roast prime rib to jambalaya. Ask a local, and they'll likely tell you that neglecting Bandera's famous cornbread is an unforgivable mistake. The Western-style interior offers a cozy respite, especially on "brisk" winter afternoons. The authentic wood-burning stove is a nice touch.
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Bijan's Bistro

633 N State St, Chicago, IL 60610 312-202-1904

Description: RIVER NORTH. Serving both food and drink until the wee hours, this New American bistro has become a popular spot, especially with the late-night bunch. Inside, dark woods, copper tiles, and faux antique light fixtures establish a comfy setting, and the menu has plenty of variety, thanks to appetizers, specialty salads, soups, sandwiches, and poultry, beef, and seafood entrees. Try barbecued chicken or a fresh-ground burger with hand-cut fries to bolster your energy.
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Boston Blackie's

164 E Grand Ave, Chicago, IL 60611 312-938-8700

Description: RIVER NORTH. In the mood for a thick burger and a pile of fries washed down with a cold beer? Head to Boston Blackie's, where you won't find a hint of pretension. Here, the friendly waitstaff and bartenders happily serve up potato skins, onion rings, burgers, and bottled and on-tap beer to eager patrons. If you're planning on hanging out later in the evening, get there before 10pm ­ closing times can vary.
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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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Cheesecake Factory

875 N Michigan Ave, lower level, Chicago, IL 60611-1803 312-337-1101

Description: MAGNIFICENT MILE. You'll face an important decision when you arrive here, so allow plenty of time to ponder before choosing your cheesecake flavor from the list of 34 decadent options. There's also a large dinner menu with plenty of great dishes and other desserts, but the obvious draw is cheesecake. Try white chocolate raspberry truffle, chocolate mousse, or double chocolate upside down Jack Daniels varieties. The dining room fills up quickly, so go early or late. EL: Red Line to Chicago
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Deca Restaurant + Bar

160 E Pearson St, The Ritz-Carlton, Chicago, 12th floor, Chicago, IL 60611 312-573-5160

Description: MAGNIFICENT MILE. This elegant, welcoming restaurant offers an inviting art-deco interior and a lovely view of Chicago's skyscrapers and the hotel fountain. As such, it's a charming spot throughout the day and night. The brasserie-inspired menu features an abundance of soups, salads, and appetizers; main courses include the Berkshire pork chop with buttered spaetzle, beef bourguignon and soft shell crab.
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Ghirardelli Ice Cream & Chocolate Shop

830 N Michigan Ave, Chicago, IL 60611 312-337-9330

Description: MAGNIFICENT MILE. Famous Ghirardelli chocolate, made by the Italian chocolate maker, is served in upscale style at this Chicago favorite. The place serves plenty of ice cream drinks, along with amazing hot fudge sundaes and a dish called "Strike it Rich" that's as decadent as it sounds. This is also the perfect place to buy a souvenir; vast assortments of chocolates are boxed and ready to give ­ or keep.
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Joe's Seafood, Prime Steak & Stone Crab

60 E Grand Ave, Chicago, IL 60611 312-379-5637

Description: RIVER NORTH. This classic dinner club-style restaurant boasts a vaulted ceiling, dark wooden furniture, and excellent lighting, making it an ideal place for a power lunch or entertaining important clients. Partner of the famous Joe's Stone Crab in Miami, this River North gem features a selection of fresh seafood and steaks. Of course, rumor has it that the stone crab claws alone are worth the trip.
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NoMi

800 N Michigan Ave, Park Hyatt Chicago, 7th floor, Chicago, IL 60611 312-239-4030

Description: MAGNIFICENT MILE. This restaurant offers an impressive view of the city as well as an upscale, elegant environment. Start off with peeky toe crab salad or a scallop tart. Next, order monkfish brochette, wild striped bass, or even the always-enticing veal strip loin. A full bar offers a vast array of wines and liquors. For added glamour, experience the romance of outdoor terrace dining by candlelight when the weather's pleasant.
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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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Pops for Champagne

601 N State St, Chicago, IL 60657 312-266-7677

Description: RIVER NORTH. This long-lived live music club and champagne bar (25-plus years!) is a city mainstay, now relocated from its original Lake View neighborhood. A sleek, stylish bar lets patrons sip and mingle, while a downstairs lounge envelops folks in intimate surroundings and terrific live jazz. The shop sells sparkling wines and offers lunchtime and light evening fare, including scrumptious housemade desserts like brown butter cheesecake, mini tarts, and chocolate fondue with berries. A raw bar and caviars are included in the upscale offerings, and more than 125 champagnes are available. Jazz sets begin at 9pm.
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RL

115 E Chicago Ave, Chicago, IL 60611 312-475-1100

Description: MAGNIFICENT MILE. Owned by fashion guru Ralph Lauren, this contemporary American restaurant has a cosmopolitan air about it. Rich leather furniture, mahogany paneling, and chic African style prints define the decor. The menu is just as fashionable and features notable items like Alaskan halibut, jumbo sea scallops in a cucumber-tomato salad, Amish chicken, and grilled lamb.
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Saloon Steakhouse

200 E Chestnut St, Seneca Hotel, Chicago, IL 60611 312-280-5454

Description: STREETERVILLE. A great alternative to Chicago's tonier (and more expensive) steakhouses, Saloon is situated a block off Michigan Avenue. The decor is suitably masculine and clubby with lots of dark wood, and service is knowledgeable and efficient. Although the menu ventures into non-beef territory, steaks are the big draw ­ if you have a big appetite, by all means order the 24-oz. "cowboy-cut" bone-in rib-eye. That's a lot of meat! After your meal, plan to enjoy a 10-oz. martini and a cigar in the bar.
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Seasons Restaurant & Lounge

120 E Delaware Pl, Four Seasons Hotel Chicago, 7th fl, Chicago, IL 60611 312-280-8800

Description: MAGNIFICENT MILE. This upscale hotel dining room pampers guests and makes them feel like royalty. The setting is elegant, boasting fresh flowers, crystal, and mahogany at every turn. The lofty location provides for great views of the cityscape below, and the menu is contemporary American with French influences. Possible entrees include Peking duck breast with wild French asparagus, clay pot-cooked Alaskan halibut with Chinese sausage, and Mediterranean Colorado lamb rack with tagine sauce. Look for seasonal specials as well as a tasting menu. The lounge provides a stylish setting for lunch, afternoon tea or cocktails.
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Signature Room at the 95th

875 N Michigan Ave, John Hancock Tower, Chicago, IL 60611 312-787-9596

Description: MAGNIFICENT MILE. If you haven't wined or dined at The Signature Room yet, your next trip will undoubtedly have to include this Chicago landmark. The high-stepping destination is a place not only to see and be seen but also to take in the beauty of the city with a 360-degree bird's eye view. Nurse a martini and laugh over the fact that you didn't make it to the Sears Tower. The menu features traditional American cuisine.
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The Café

120 E Delaware Pl, Four Seasons Hotel Chicago, 7th fl, Chicago, IL 60611-1443 312-649-2349

Description: GOLD COAST. An offshoot of the popular, more upscale Seasons, this café offers similarly great food at more reasonable prices and in a more relaxed environment. American favorites are the specialty, and plenty of sandwiches, salads, pastas, and beef dishes satisfy any appetite. The dining room is cool and peaceful, and service is friendly and attentive. A prix fixe dinner is $35.00
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The Capital Grille

633 N Saint Clair St, Chicago, IL 60611 312-337-9400

Description: MAGNIFICENT MILE. One of the many reasons The Capital Grille has become a carnivore's mecca for Chicagoans and visitors alike is the melt-in-your-mouth, dry-aged in-house beef. Everything from the signature Veal Chop with Roquefort butter sauce to Steak au Poivre with Courvoisier cream is tantalizing. "Wine Spectator" magazine granted The Grille a "Best of Award of Excellence" for their 300-bottle wine list. The decor is simple yet elegant with Tiffany lamps, sumptuous carpeting, rich brown and forest green hues, and large windows. A lovely wine room is available for private events and occasionally serves as an additional bar.
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The Grill on the Alley

909 N Michigan Ave, Westin Michigan Avenue, Chicago, IL 60611 312-255-9009

Description: MAGNIFICENT MILE. Designed in the style of the famous Grill on the Alley in Beverly Hills, this restaurant is a favorite with the Michigan Avenue crowd, who stop in for quick bites during shopping excursions. The Grill offers a diverse menu that features Cobb salads and other light fare, as well as Chicago-style steaks and delicious specials. After hours, well-heeled patrons flock to the bar to nip on martinis, single malt scotches, and fine wines.
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The Lobby

108 E Superior St, The Peninsula Hotel, Chicago, IL 60611 312-573-6760

Description: RIVER NORTH. Come for breakfast, lunch, high tea, dinner, or dessert, and enjoy expansive views of the city's bustle from grandly proportioned windows. Extensive breakfast options range from traditional standards to decadent Nutella-stuffed French toast with banana brulee and "Nasi Goreng" Balinese fried rice with eggs and chicken satay. Live cello and piano music are available in the evenings. Note to chocolate-lovers: A buffet bar serves up the richest treats with coffees every Friday and Saturday night giving you energy to dance the night away while a contemporary jazz trio and singer perform.
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Tru

676 St. Claire St, Chicago, IL 60611 312-202-0001

Description: STREETERVILLE. An evening at Tru presents posh dining in elegant, simple surroundings. The bar serves over a dozen varieties of champagne by the glass, perfect for priming the palate. Expect to spend at least two hours at a dinner that constantly elevates your tastes. Three-course tasting menus may include salmon mousse with chilled tomato soup, tender veal with artichokes in a lush napoleon, and lobster prepared three ways: lobster bisque, lobster mushrooms, and lobster salad. A sommelier is on hand to assist with wine selections, and service is unparalleled.
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