6 Things You Absolutely Must Do In Chicago

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Planning your next getaway to the Windy City? Here’s how to make it unforgettable: from skyline views and deep dish pizza to iconic landmarks and unforgettable experiences.

Whether you’re visiting Chicago in the sunny days of summer or the snow-covered charm of winter, there are plenty of places to go, foods to eat, and things to experience in this vibrant city full of iconic experiences, delicious eats, and world-class entertainment.

With so many options, it’s easy to get overwhelmed trying to decide what to add to your itinerary. Not sure where to start?

Here are six things you absolutely must do while you’re in Chicago:

1. Take in the Skyline Views from Above

Start your trip with a stunning look at the city from the clouds! The Skydeck at Willis Tower is Chicago’s most famous observation deck—and stepping onto The Ledge is a thrill you won’t forget. But it’s not the only spot to admire the view.

Book a table at Cindy’s Rooftop for incredible views with brunch, lunch, or dinner, or grab tickets to 360 CHICAGO at the John Hancock Center, where you can brave TILT, a one-of-a-kind thrill ride that literally tilts you out over the city.

2. Catch a Game at Wrigley Field

Baseball fan or not, Wrigley Field is a bucket-list-worthy experience. Home to the Chicago Cubs, this historic stadium is full of charm, energy, and good old-fashioned fun.

Enjoy classic ballpark food, cheer with the locals, and maybe even catch a foul ball if you’re lucky. It’s a true slice of American tradition, right in the heart of the city.

3. Explore the Art Institute of Chicago

Love art? Don’t miss the Art Institute of Chicago—one of the oldest and largest art museums in the U.S. Wander the galleries and take in iconic works like American Gothic by Grant Wood and A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat (Ferris Bueller fans, you’ll recognize it instantly!).

With ever-changing exhibitions and an impressive permanent collection, it’s easy to lose track of time here.

4. Eat a Classic Chicago-Style Hot Dog

No trip to Chicago is complete without sinking your teeth into a Chicago-style hot dog. This unique creation features an all-beef dog on a poppy seed bun, topped with yellow mustard, chopped onions, sweet pickle relish, tomato slices, a dill pickle spear, sport peppers, and a dash of celery salt—never ketchup.

Grab one from Portillo’s or head to Superdawg Drive-In, the last of its kind in the city, for a side of retro vibes with your dog.

5. Spend Time in Millennium Park

This lively downtown spot is a must-visit no matter the season. Millennium Park is home to the famous Cloud Gate (aka “The Bean”) and hosts everything from free summer concerts to festive winter ice skating.

You’ll also find splash fountains, gardens, public art, and wide open spaces to relax or people-watch. It’s the perfect stop whether you’ve got kids in tow or just want to soak in the local atmosphere.

6. See a Comedy Show at The Second City

If you love to laugh, The Second City should be high on your list. This legendary improv theater has launched the careers of countless comedy icons like Tina Fey, Stephen Colbert, and Bill Murray.

Check the schedule while you’re in town and grab tickets for a show—you never know when you’ll be watching the next big star.

Even More Things to Do in Chicago

Still looking for more fun? Here are a few bonus ideas to round out your Chicago itinerary:

Navy Pier
With rides, shops, restaurants, and an iconic Ferris wheel overlooking Lake Michigan, Navy Pier is fun for the whole family. In the summer, don’t miss the free fireworks shows on Wednesday and Saturday nights!
Walk the Chicago Riverwalk
This scenic pedestrian path along the Chicago River is perfect for a relaxing stroll, outdoor dining, or hopping on a boat tour. Architecture lovers will especially enjoy a Chicago Architecture Cruise, which offers a unique perspective of the city’s skyline.
Visit the Museum of Science and Industry
One of the most engaging science museums in the world, this spot is perfect for curious minds of all ages. Explore interactive exhibits, climb aboard a real submarine, or watch a tornado form right before your eyes!
Try Deep Dish Pizza
You can’t leave Chicago without digging into a slice of deep dish pizza. Head to Lou Malnati’s, Giordano’s, or Pequod’s to get your fix of cheesy, saucy, buttery-crusted goodness. (Pro tip: it’s super filling—one slice might be enough!)

Did your favorite Chicago attractions make the list? If not, I’d love to hear your picks! Leave a comment and let me know what spots everyone absolutely must check out on their next Chicago adventure.