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10 Delicious Dining Destinations in Chicago

Hungry for a new travel destination? Check out our guide to the 10 dining hotspots in Chicago that are guaranteed to satisfy even the deepest(dish) appetite.

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1. Sixteen

1. Sixteen

Michelin-rated and chosen by Zagat as one of the 10 top restaurants with a view in Chicago, Sixteen offers a spectacular dining experience within the Trump International Hotel & Tower. Overlooking the city from the 16th floor, the restaurant’s 30-foot floor-to-ceiling windows give visitors an unparalleled panorama of Chicago’s famed skyline. Whether you’re planning a romantic dinner, celebrating a special occasion, or looking for a high-end meal that you won’t soon forget, you’ll be well taken care of at Sixteen. Waiters are attentive and knowledgeable about the eclectic menu and vast wine cellar. Sample the assortment of fine appetizers that includes burgundy snail risotto, raw sliced hamachi, or chilled lobster salad. The entrées further live up to Sixteen’s stellar reputation. Wild sockeye salmon, prime New York strip and seared duck breast share the menu with pork tenderloin, fresh Alaskan halibut and bacon-wrapped monkfish. And dessert lovers – be prepared to indulge. Take delight in the tart cherry shortcake, or gianduja chocolate cremeux. Sixteen offers first-class dining in a picturesque setting and is open for breakfast, brunch, lunch as well as dinner. (Photo courtesy of Trump International Hotel and Tower, Chicago)

(401 North Wabash Avenue,

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2. Charlie Trotter's

2. Charlie Trotter’s

Rated as one of the world’s top 50 eateries by Restaurant Magazine in 2007, Charlie Trotter’s exudes culinary elegance. The restaurant and its eponymous chef believe that their clientele deserve the freshest, most exquisite meals possible. Instead of overpowering the palates of diners with rich sauces and heavy portions, Trotter prefers to serve a series of small courses – each one complimenting the next. His tasting menu approach allows guests to savour true flavour. Using each season’s finest ingredients, the meal selection is constantly evolving. Menu courses change daily. This spontaneity brings cuisine to the table that is always delicious, never boring. Charlie’s repertoire has included steamed Maine Diver scallop with Manila clams and spring peas, green garlic gnocchi with red mustard leaves and celery root, and Elysian Fields lamb with smoked red pepper. Fresh, inventive and satisfying. Indulge your senses and experience the gourmet creations of one of Chicago’s most celebrated chefs. (Photo by Battman, courtesy of Charlie Trotter’s)

(816 West Armitage Ave.,

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3. Gibsons Bar and Steakhouse

3. Gibsons Bar and Steakhouse

If you prefer your steaks extra-large on taste and portion size, Chicago is a meat lovers paradise. Many steakhouses brag about their excellent beef, but Gibsons Bar and Steakhouse is the only restaurant group in the United States to have its own USDA Prime Certification. Their USDA Gibsons Prime Angus beef hails from local, sustainable farms. Corn-fed and then aged for 40 days, the result is unrivalled succulent flavour. Choose from Filet Mignon, Bone-in Sirloin, T-Bone or Porterhouse, all cooked to juicy perfection. Add to your enjoyment with a wide array of mouth-watering soups, salads and side dishes – if you have room. Gibsons doesn’t believe in cutting corners. All portions whether entrées, sides or desserts are massive. With their stellar reputation for scrumptious meals and refreshing cocktails, it’s hardly surprising that Gibsons is a favourite of the rich and famous. Be sure to study the wall of fame for autographed photos of athletes, actors, politicians and musicians. Dine inside amidst the warm ambience, or relax outside on the popular patio – perfect for people watching along bustling Rush Street. (Photo courtesy of Gibsons Restaurant Group)

(1028 North Rush Street,

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4. Pizzeria Uno

4. Pizzeria Uno

A visit to the Windy City is not complete without sampling their famous deep-dish pizza. Invented at Chicago’s Pizzeria Uno in 1943, this cheese and tomato extravaganza defies its Italian roots. Unlike its thin-crusted Roman kin, the Chicago-style pizza more closely resembles a pie baked in a deep, round pan. The crust is high, thick and crunchy – like a buttery biscuit. Gooey layers of mozzarella intermingle with overly generous portions of spicy pepperoni and sausage, zesty onions and savoury mushrooms. Topped with ladle upon ladle of freshly puréed tomato sauce, the purpose of the heavy crust becomes clear – it locks in the abundance of ingredients. The traditional deep-dish pizza recipe may have been created over 60 years ago, but it’s still the meal of choice at its birthplace, Pizzeria Uno. If your hunger can’t withstand Uno’s long lines, try its sister restaurant Pizzeria Due, Lou Malnati’s, or Gino’s East. Be warned – a small pizza pie can easily satisfy the largest of appetites. (Photo copyright of City of Chicago/GRC)


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5. Chicago-Style Hot Dogs

5. Chicago-Style Hot Dogs

Move over deep-dish pizza, there’s another Chicago institution vying for table space. The Chicago-style hot dog, piled high with brightly hued condiments and vegetables has a lengthy history. Legend has it that the hearty wieners originated in 1893 when Samuel Ladany and Emil Reichl, immigrants from Austria-Hungary, began selling their kosher, all-beef sausages in Chicago. By 1929, Fluky’s, a local grocer gave the meal a makeover. Nicknamed the ‘banquet on a bun’ or the ‘depression sandwich,’ the famous fare adopted the look it still boasts today. Served on a soft, yet sturdy poppy seed bun, the boiled wiener is dressed with colossal amounts of yellow mustard, fluorescent green sweet pickle relish, white onion, tomato chunks, dill pickles, spicy whole peppers and a dusting of celery salt. How serious do Chicagoans take their dogs? Condiments are strictly applied in this order and ketchup is never included. With over 1,800 hot dog stands populating the city – more than all the McDonald’s, Wendy’s and Burger King franchises combined – the hot dog continues to reign as king of Chicago appetites. Try these tasty, overloaded dogs at Fluky’s, Superdawg, or via the many hot dog carts doting the city sidewalks. (Photo copyright of City of Chicago/GRC)

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6. Hugo's Frog Bar & Fish House

6. Hugo’s Frog Bar & Fish House

Seafood fans, your ship has come in at Hugo’s Frog Bar & Fish House. This upscale restaurant prides itself on its extensive seafood menu. Receiving fresh fish several times daily, Hugo’s guarantees that only the best, most luscious food is served. Impressive doesn’t begin to describe this seafood selection: sautéed soft shell crabs in lemon butter, grilled wild salmon, miso marinated sea bass, Oysters Rockefeller, Alaskan King Crab and their signature dish, frog legs with garlic butter. Love lobster? You’re in luck. Hugo’s brings you a smorgasbord of melt in your mouth dishes. Try their giant Australian lobster tails, spicy lobster cocktail or a whole Maine lobster – many tipping the scales at 5 pounds each. Hugo’s also showcases one of Chicago’s native dishes, Shrimp de Jonghe. A buttery casserole of whole shrimp nestled in a bed of garlic-infused bread crumbs, this delicacy dates back to late 19th century Chicago. Portions at Hugo’s are enormous, so be sure to arrive with a huge appetite to conquer your catch of the day. (Photo courtesy of Gibsons Restaurant Group)

(1024 North Rush Street,

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7. Sprinkles

7. Sprinkles

When Oprah Winfrey loves your cupcakes, you know that you’re in good company. Yes, Chicago’s most popular celebrity adores Sprinkles, the home of decadent cupcake treats. Pastry chef Candace Nelson first brought Sprinkles to life in Beverly Hills. What started out in 2005 as the world’s first bakery devoted solely to the creation of cupcakes, now boasts 11 shops across the United States, including the busy Chicago location. Baked daily in the store, Nelson’s confections are handcrafted using only quality ingredients including sweet cream butter, pure vanilla and Callebaut chocolate. It’s easy to see why Chicagoans are addicted. The moist cake and creamy icing put their competitors to shame. With over 20 flavours and many seasonal recipes celebrating holidays, devotees are spoilt for choice. Amuse your taste buds with chocolate marshmallow, cinnamon sugar, strawberry, lemon coconut, or peanut butter chip cupcakes. Sprinkles also offers vegan and gluten-free versions of their #1 best seller, the red velvet cupcake. Don’t be surprised if you discover line-ups streaming out the door on East Walton Street. One bite and you will be hooked – just like the rest of Chicago. (Photo courtesy of Sprinkles Cupcakes)

(50 East Walton Street,

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8. Sarah's Pastries and Candies

8. Sarah’s Pastries and Candies

Visited by Martha Stewart and celebrated by Rachael Ray and Bride’s magazine, Sarah’s Pastries and Candies is much more than your typical candy emporium. Born and raised in Chicago, Sarah Levy conveyed her love of all things sweet and decadent into this delectable business in 2004. Not content on selling pre-packaged treats, she crafted her own chocolate candies and truffles, flakey pastries, fresh fruit tarts and pies, cookies and elegant cakes. The result? Her boutique on Chicago’s fashionable Oak Street was a smashing success. With foodie fans raving about her freshly baked products and delicious guilty pleasures, she expanded her menu to include gourmet sandwiches, specialty coffees and teas as well as extravagant gift baskets – all products made by chefs on the premises. Now with a second shop conveniently located within Macy’s on State Street, patrons can easily satisfy their cravings while on the go. Don’t miss the morning pastries – chocolate croissants and crème fraiche coffee cake are favourites – or the lunch-time sandwiches. Sarah’s got something cooking for all tastes. (Photo by Stephen Hamilton, courtesy of Sarah’s Candies)

(70 East Oak Street and Macy’s 111 North State Street,

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9. Harry Caray's

9. Harry Caray’s

If you’re looking for a sophisticated dish native to Chicago, try Chicken Vesuvio. An Italian meal beloved by diners and food critics alike, Chicken Vesuvio is both hearty and mouth-watering. Mysteriously, no one seems to recall how or why the city came to claim this recipe as its own. Chicago chefs point to the fact that genuine Italian cookbooks fail to depict a meal resembling Vesuvio – and they’re more than happy to declare ownership. Despite its puzzling history, Chicagoans have adored this combination of chicken and vegetables for decades. They savour the crisp, golden skin which gently gives way to the tender meat underneath. Infused with a tasty mixture of olive oil, white wine, oregano and garlic, the baked chicken is juicy and flavourful. Pan-roasted potatoes and fresh peas complete this succulent dish. Phil Vettel, restaurant critic for the Chicago Tribune, chose the Chicken Vesuvio at Harry Caray’s Italian Steakhouse as the best in the city. Housed in one of the most historically significant buildings in Chicago – Al Capone’s mob used the venue for their bootlegging activities – Harry Caray’s offers a memorable and delicious dining experience. (Photo courtesy of Harry Caray’s Restaurant Group)

(33 West Kinzie Street,

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10. The Taste of Chicago

10. The Taste of Chicago

Fancy strolling beside Chicago’s beautiful lakefront while enjoying delicious food? The Taste of Chicago takes a bite out of the city every summer. This year 59 restaurants participated, feeding an estimated 2.35 million hungry foodies over the 10 day festival. Grant Park hosts this annual free-admission event where visitors can sample steak tacos, baby back ribs, mustard fried catfish, pad thai, jerk chicken and Chicago-style hot dogs. Want to try orange chicken, beignets or a mini steak jibarito? Just purchase a strip of ‘Taste Tickets’ for $8 and the feasting begins. True to Chicago’s hospitable nature, the meals on offer are large and plentiful. This year’s celebrations saw over 20,000 cheeseburgers served by the Billy Goat Tavern while Eli’s Cheesecake dispensed 50,000 cake slices. Musical entertainment, cooking and fitness demonstrations, plus a huge playground area round out the festive atmosphere. And if you’re still hungry in the evening, the Gourmet Pavilion dishes out upscale cuisine from Chicago’s premiere restaurants. Bring sunscreen, comfortable shoes and your appetite to soak up the flavours that make Chicago a must-visit dining destination. (Taste of Chicago runs late June – early July each summer). (Photo copyright of City of Chicago/GRC)