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A Culinary Tour

Chicago’s culinary scene has exploded in the past decade, leaving in its wake a tantalizing selection of top-notch eateries, restaurants and bars at seemingly every turn. The city’s trademark cuisine is a delightful mash-up of classic Midwestern comfort foods, many with an ethnic twist, and cutting-edge gastronomy prepared by award-winning chefs. For a truly authentic taste of Chicago, you’ll want to sample the full spectrum — everything from ballpark-style hot dogs to the rarest imported Wagyu steak.

Day

1

MORNING
  • Have Brunch over the Water.

    Chicagoans are so brunch-centric that most establishments offer it on both Saturdays and Sundays, but nowhere as visually spectacular as at GreenRiver. Perched on the 18th floor, this Michelin-star restaurant serves exquisite items like Brioche Pain Perdu made with peaches, vanilla bourbon and pecans, alongside panoramic views of cobalt-blue Lake Michigan and the silver city skyline. 

MIDDAY
  • See Wrigley Field Up Close.

    The Windy City is home to not one but two Major League Baseball teams, including the 2016 World Series winner, the Chicago Cubs. The Cubbies’ stadium, Wrigley Field, was built in 1914, and is one of the last old-time baseball stadiums left in the nation. Daily tours take you behind the scenes of this beloved cultural icon, from the press box to the dugout. 

  • Try an Authentic Chicago Dog.

    Down the street from Wrigley Field, Wrigleyville Dogs serves classic Chicago-style hot dogs: 100 percent pure Vienna beef on a poppy seed bun slathered in yellow mustard, relish, onion, tomato, pickle and hot peppers, with a dose of celery salt. 

AFTERNOON
  • Taste the Mag Mile Sweets.

    Head to Chi-Town’s swanky shopping district on Michigan Avenue, known as the Magnificent Mile, to sample turmeric- and ginger-infused chocolate bars, among other treats, at Vosges Haut-Chocolat, Chicago’s own designer chocolatier. Be sure to pay your respects to Garrett’s, a Chicago institution that has been selling outrageously good gourmet popcorn since 1949. Order the Garrett Mix, a salty-sweet combination of cheese corn and caramel corn.

  • Meet Sue.

    Three of Chicago’s most famous museums sit side by side at the aptly named Museum Campus, including the state-of-the-art science museum known as the Field. Here, you can gaze up at Sue, the largest, best-preserved and most complete Tyrannosaurus rex fossil ever found, spanning 40 feet from snout to tail. Snag a fresh cup of joe inside the museum at the Field Bistro or an ice-cold pint of Tooth & Claw, Sue’s signature beer. 

EVENING
  • Indulge the Purple Pig.

    Dine like an in-the-know Chicagoan at the Purple Pig, the darling of the trendy River North neighborhood. This cozy James Beard Award-winning eatery dishes up succulent small plates with big-time flavor. Think: chamomile-tea smoked pork leg steak, house-cured sardines on toast, and octopus with salsa verde. 

  • Choose Your Music.

    With two world-class music clubs literally around the corner from each other, you might not have to pick just one. Buddy Guy’s Legends, made famous by namesake Grammy-winning guitarist Buddy Guy, is the home of blues. Jazz Showcase has been proudly presenting the greatest jazz in Chicago since 1947. Both venues host live shows every night of the week.  

Day

2

MORNING
  • Eat Gourmet Doughnuts.

    Start the day at Firecakes Donuts, where fried dough reaches new levels with all-natural ingredients and artisan touches like imported cocoa from France. Get Sicilian Pistachio Old Fashioned if it’s in season; otherwise, opt for Butterscotch Praline.  

  • Visit the Bean.

    Chicago’s immense lakefront park system knows no equal among the world’s major metropolises. The innovative design dates back to 1909, when forward-thinking civic designers decided to reclaim the lakefront for the public. At Millennium Park, Chicago’s newest, you’ll find the city’s most photographed piece of public art, known locally as “the Bean,” for its kidney-bean shape. The 110-ton steel sculpture’s actual name is “Cloud Gate,” by British artist Anish Kapoor. And yes, you’re supposed to touch its mesmerizing mirrorlike surface. 

MIDDAY
  • Dig into a Deep-Dish Pizza.

    Opened by the son of Rudy Malnati, the man largely responsible for creating the famous Chicago-style deep-dish pizza, Lou Malnati’s Pizzeria has grown to become the quintessential Chicagoland pizza chain. While there are thin-crust pizzas available at Lou Malnati’s, it’s practically a crime not to choose a big, juicy deep-dish on a first visit. 

  • Visit the Top Museum.

    With more than 300,000 works displayed in 1 million square feet, the Art Institute of Chicago is the second largest in the country, behind New York’s Metropolitan Museum of Art. Don’t miss “American Gothic,” a national art treasure. Weather permitting, enjoy a glass of rosé on the terrace at Terzo Piano on the third floor of the modern wing. 

AFTERNOON
  • Hop Aboard.

    Take in a whopping 50 famous landmark buildings along the Chicago River on a cruise with the Chicago Architecture Foundation. The 90-minute tours depart every hour on weekends. Purchase your ticket at Chicago’s First Lady boat dock.

EVENING
  • Experience the Top Chef.

    Rick Bayless, the Top Chef Masters Winner in 2009, owns a block of restaurants downtown, including three Mexican-style establishments in the same building on North Clark Street. Depending on preference, diners can choose from Bayless’ flagship Frontera Grill; the artsy, sophisticated Topolobampo; or his take on street food, the fast-casual XOCO. 

  • End with a Nightcap.

    On the 12th story of The Ritz-Carlton, Chicago, overlooking the Magnificent Mile, you’ll find the ultra-modern Rooftop at Torali, a captivating venue for cocktails with a view.