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The Top 10 Things to Do in Chicago

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The Cubs finally won the World Series – after a 108-year drought – in 2016, but the celebratory buzz will likely remain for a long time to come. Catching a game at Wrigley Field, baseball’s second-oldest stadium after Boston’s Fenway Park, is certainly one of the top things to do in Chicago, as is visiting its museums, lakefront parks, funky neighborhoods and architecturally rich buildings – not to mention trying its deep-dish pizza and other local treats.

Things to do in Chicago


 One of Chicago’s grandest boulevards is North Michigan Avenue – specifically a stretch called Magnificent Mile. Here you’ll find AAA Five Diamond Rated luxury hotels including The Peninsula and The Waldorf Astoria, as well as boutique lodging options like The Kinzie, which offers modern design, skyline views and room service by The Public House gastropub. Designer shopping is all around, and there’s certainly no shortage of trendy restaurants with options like The Purple Pig nearby, serving up wine, cheese, in-house made charcuterie and tapas-style fare.

Magnificent Mile at dusk.


 An essential part of Chicago travel is a visit to Millennium Park to see Cloud Gate, the beloved Anish Kapoor-designed, bean-shaped stainless steel sculpture. It’s highly reflective surface captures the skyscrapers behind it in the most Instagrammable way. Of all the things to do in Chicago, it is one of the most photographed. Every day Millennium Park offers a variety of free programs, festivals and exhibitions, and you might even catch a concert at the Jay Pritzker Pavilion. Be sure to check what’s happening before you go.

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The Art Institute of Chicago is a can’t-miss attraction. The massive museum is home to several national treasures including “American Gothic” by Grant Wood and “Nighthawks” by Edward Hopper.

Top photo: Deep-dish pizza is a Chi-Town staple. (Photo: Thinkstock)


The Navy Pier is the perfect place to go for a walk, catch a river cruise and get a taste for all the city has to offer. Kids will love taking a ride on the Centennial Wheel – offering 360-degree views of the skyline and Lake Michigan – and trying the hands-on exhibits at the Chicago Children’s Museum. Restaurants along the pier feature favorites such as Chicago-style Dogs at America’s Dog and deep dish pizza at Giordano’s. And if you have time for more exploring, check out the Crystal Gardens indoor botanical garden.


A great way to see Chicago’s legendary architecture (the world’s first skyscraper, the Home Insurance Building, was built here in 1885) is to sign up for a guided boat tour along the Chicago River. For a different vantage point, head to the top of the John Hancock Building to experience the 360 Chicago observation deck. Those truly unafraid of heights can ride Tilt – a moving platform that tilts you downwards, 94 stories above the city.


Catch a game at Wrigley Field. Dating from 1914, the iconic stadium is known for its ivy-covered brick outfield wall, rooftop bleachers and red marquee sign over the main entrance. Grab tickets for a tour for a chance to step onto the field, sit in the dugout and learn all about the history of the ballfield. For pregame excitement or post-game celebrations, hang out with fellows Cubs fans at one of the dozens of bars in Wrigleyville. The Cubby Bear is a classic that’s been around for over 60 years.


 Visit Sue, the world’s best-preserved Tyrannosaurus rex skeleton at the Field Museum of Natural History, which boasts plenty of other dazzling artifacts and specimens in its vast collection. At the Museum of Science and Industry, you and your family can explore the most amazing aspects of the natural world and innovations with exhibits like “Science Storms,” which features a 40-foot tornado that you can control. Or learn the history of the Windy City at the Chicago History Museum, where visitors can sit on Chicago’s very first L car, among many other interesting hands-on and interactive exhibitions.


 Deep-dish pizza and Chicago hot dogs are staples of any Chicago travel adventure, but you can also try the food truck scene. Fat Shallot has sandwiches like truffle BLTs and the Slide Ride sells gourmet sliders.


 The city has no shortage of fine dining restaurants, including many that are AAA Diamond Rated. The AAA Five Diamond Alinea, helmed by highly creative chef Grant Achatz, serves New American tasting menus. Newly remodeled and reopened in May 2016, all three experiences offered – from the intimate kitchen table, reserved for parties of 6 only, to the more approachable salon menu – are unforgettable and worth the splurge.


An elegant spot to have a cocktail is The Bar at the Peninsula Hotel. Long a favorite of celebrities and local pro athletes, the dimly lit lounge has a large selection of martinis and single malt whiskeys.

Which of these things to do in Chicago would you like to try? Tell us in the comments.

Looking for a variety of great lodging options in the area? Find and book great hotels in ChicagoCall 1-800-873-8283 to speak to a AAA travel counselor today or click here.


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