The Best Things to do in Chicago
By Jamie Dutton
Chicago, a city of broad shoulders and even broader tastes, is brimming with things to do. Whether you're into art, history, or eating your way through a 3,000-calorie pizza, the Windy City has something to keep you entertained. Here are five must-do experiences that capture the spirit of Chicago.
1. Millennium Park
Millennium Park is more than just a park—it's a selfie battleground, and Cloud Gate (lovingly dubbed "The Bean") is the ultimate prize. Every visitor tries to capture the perfect distorted reflection of the skyline and their faces, and it's amusing to watch people maneuver for the best angle. It’s also a great spot to enjoy some public art, relax by the Crown Fountain, or catch a concert at the Jay Pritzker Pavilion, which doubles as a giant stainless-steel band shell.
2. Art Institute of Chicago
No trip to Chicago is complete without visiting the Art Institute of Chicago. Home to Grant Wood’s "American Gothic" and George Seurat’s "A Sunday on La Grande Jatte," it's like stepping into an art history textbook, except no one's going to quiz you on the way out. I could spend hours wandering the impressionist galleries, losing myself in a Monet haze. If you’re into medieval armor or miniature rooms, they've got those too—because why not?
3. Wrigley Field
Even if you don't know a baseball from a basketball, a visit to Wrigley Field is essential. The stadium is a relic of old-time Americana, complete with ivy-covered outfield walls and hot dogs that require an immediate run around the bases just to burn off the calories. Catching a Cubs game here is less about the score and more about soaking in the atmosphere. It’s where you can truly experience the essence of Chicago sports culture—loud, proud, and never quite sober.
4. Willis Tower Skydeck
Once known as the Sears Tower, the Willis Tower Skydeck offers views that will make you question why you ever thought about conquering your fear of heights. The real thrill is "The Ledge," a glass box that extends out 4.3 feet from the 103rd floor, giving you the sensation of floating above the city. It's a surreal experience, assuming you can manage not to look down too long or scream loud enough to shatter the glass.
5. Navy Pier
Sure, it’s a little touristy, but Navy Pier has its charms. With a giant Ferris wheel, boat tours, and an endless supply of fried food, it’s like a carnival that got lost on its way to the Midwest and ended up on the shores of Lake Michigan. The Chicago Shakespeare Theater is here too, in case you need a little culture to balance out the funnel cakes. It’s the kind of place where you can spend the day pretending you’re on vacation, even if you’re only a few miles from home.
The Complete Guide to Chicago
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Chicago’s hotel scene is an adventure worthy of a trip to the Windy City alone. From iconic skyscrapers to tucked-away gems, the city’s lodgings cater to every kind of traveler, from the lavish to the low-key.
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Chicago, the Windy City, is many things: a cultural mecca, a sports hub, and a town that takes its food very, very seriously. From deep-dish debates to avant-garde tasting menus, there’s a little something here for every palate.
Best Things to do in Chicago
Whether you're into art, history, or eating your way through a 3,000-calorie pizza, the Windy City has something to keep you entertained. Here are five must-do experiences that capture the spirit of Chicago.