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Chicago Travel Essentials

Updated: Dec 8, 2021

Read on to find out about some Chicago travel essentials, top attractions, and events to put on your itinerary.

Chicago is a sparkling winter wonderland in the cold-weather months, particularly when the city is cloaked in a layer of fluffy snow. But don’t let the chilly temperatures discourage you: There’s plenty to do in Illinois’ bustling capital from November through March—from museum hopping and sipping delicious craft beverages to ice skating and sledding—so pack some layers and prepare for a stellar urban adventure.

Arts, Culture, and History

For fans of arts, culture, history, or all the above, no trip to Chicago is complete without a visit to a selection of the metropolis’ museums, which are also less crowded in the wintertime. Spend the day at the Art Institute of Chicago, a stately stone building that houses about 300,000 works of art, ranging from whimsical Impressionist masterpieces to textiles and ceramics from Asia. For a peek into the past, the Chicago History Museum, where you can learn about key moments that shaped the city, including the 1871 fire, and the Field Museum, where aspiring paleontologists can admire real life-size dinosaur skeletons, replicas of Egyptian tombs and other prized exhibits. Whether or not you’re a fan of the stage, be sure to wander around the Theatre District in downtown Chicago, an area packed with gorgeous architecture and venues playing shows of all genres, from Broadway-caliber productions to live comedy.

There are also plenty of options for families in Chicago, including the interactive-exhibit-packed Museum of Science and Industry (don’t miss a tour of the U-505 submarine); Shedd Aquarium, where 1,500 species of marine mammals, fish, snakes, insects, and amphibians thrive year-round; and the Lincoln Zoo, home to big cats, penguins, gorillas and other animals—many of which are more active in the winter months. The Chicago Children’s Museum at Navy Pier and Bronzeville Children’s Museum—the first African-American-centered museum for kiddos ages 3 to 9 in the country—are also excellent options for crews with little ones in tow.

To revel in the excitement of cheering on pro sports teams with locals, check the schedules at United Center, where NBA’s Chicago Bulls play hoops (October through April), or Soldier Field, the stomping grounds for NFL’s Bears (August through January). The Blackhawks hockey team also squares off against other NHL competitors at United Center, an arena that transforms into an ice rink for tournaments (October through April).

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If you’re craving some outdoor fun, bundle up for a stroll in Millennium Park, Chicago’s legendary town square; take a group selfie in front of the iconic reflective Cloud Gate sculpture (lovingly known as the Bean). Or show off your ice-skating moves at the park’s McCormick Tribune Plaza & Ice Rink or next door at Maggie Daley Park’s skating, which offers opportunities to glide amid snow-dusted pines and views of the skyline. Thrill seekers can partake in more powdery fun at the sledding hill at Soldier Field, an expanse featuring a 35-foot slope that’s maintained by the park district’s snow-making machines.

Chicago’s impressive roster of shopping districts—including the Magnificent Mile, one of the world’s most famous—makes it an excellent place to indulge in retail therapy. The Magnificent Mile on Michigan Avenue is lined with big-name department stores and boutiques, including luxury brands like Coach, Tiffany & Co. and Burberry. Stop at Water Tower Place to check out kid-pleasing destinations like American Girl Place, a haven for lovers of the iconic dolls, and the Lego Store, a shop offering themed kits and accessories for builders of all ages. To shop locally owned boutiques, head to Wicker Park and Bucktown for eclectic finds and Andersonville and Lincoln Park for handmade art and jewelry and vintage collections.

Once you’ve worked up an appetite, Chicago’s flourishing food scene is ready to satisfy your cravings. To cross the city’s must-eat dishes off your list, go to Lou Malnati’s (sauce-coated deep-dish pizza), Al’s Italian Beef (eponymous sandwiches stacked with roasted sirloin) Portillo’s (Chicago-style dogs topped with relish, celery salt, chopped onions, sliced tomatoes, sport peppers, and a pickle). Soul-warming craft beverages also await at bars and breweries across town, whether you’re hankering for a expertly shaken cocktail or refreshing IPA. Choose from 100 whiskeys at music-themed Delilah’s; pair Belgian-inspired bites with a local brew at Hopleaf gastropub or sip Old Fashioneds at the swanky, hidden Violet Hour speakeasy.

If you’re flying in and/or out from O’Hare International Airport, consider a stop in Rosemont, a suburb just 4 miles away. There, visitors will find a casino, the Fashion Outlets of Chicago, Kings Entertainment bowling alley and other layover-friendly fun.

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