Things To Do Chicago That Will Amaze You Today

Chicago is a city bursting with life, history, and culture. If you’re on the lookout for things to do in Chicago, you’ll find plenty of extraordinary experiences awaiting you in 2026. From world-class museums to mouthwatering cuisine, and unique performances filling the streets, there’s much to explore. Here’s a curated list of seven mind-blowing things to do in Chicago that you won’t want to miss.

## Things to Do in Chicago That Will Amaze You Today

1. Explore the Art of the South Loop

The South Loop area is home to the renowned Art Institute of Chicago, one of the oldest and largest art museums in the United States. Not only can you admire classic masterpieces by Grant Wood and Georges Seurat, but you can also delve into contemporary exhibits that spotlight local talents, like Theaster Gates. The museum frequently showcases innovative spaces that challenge traditional art, ensuring that no two visits are ever the same.

With its vast collections, you can spend hours exploring the art that tells the story of human creativity. Dive into Chicago things To do by checking out their special events or educational programs that often cater to families and children. Imagine chatting with knowledgeable docents who make art come alive as you wander through the galleries.

2. Take a Thrilling Architectural Boat Tour

What better way to appreciate Chicago’s stunning skyline than from the waters? Companies like Shoreline Sightseeing offer scenic architectural boat tours that dive deep into the stories behind famed buildings like the Willis Tower and John Hancock Center. You’ll get breathtaking views paired with fascinating storytelling about how Chicago transformed from a muddy port town into a bustling urban center.

This experience not only highlights the city’s architectural achievements but also showcases the Riverwalk, which has become a centerpiece for both locals and tourists. Keep your camera handy; those skyline photos will be frame-worthy!

3. Attend a Live Performance at Millennium Park

Millennium Park isn’t just famous for its iconic Cloud Gate sculpture, affectionately nicknamed “The Bean.” This vibrant space often hosts free live performances at the Jay Pritzker Pavilion, presenting everything from classical symphonies to indie bands. With its stunning skyline as the backdrop, there’s something magical about enjoying live music amid the greenery.

Bring a blanket and some snacks for a picnic while you soak in the local talent. Be sure to check their schedule, as you never know what amazing performances await you. It’s a great way to connect with the arts without breaking the bank.

4. Savor Deep-Dish Pizza at Giordano’s

You simply can’t visit Chicago without indulging in its famed deep-dish pizza. Giordano’s is a local institution, well-known for its buttery crust and generous layers of cheese and toppings. Originating from Italian immigrants, this stuffed pizza variety has carved out its place in the city’s culinary landscape.

Plan to settle in for a delicious meal because each slice is practically a feast! Expect to wait in line, especially during peak hours, but rest assured, the heavenly taste will be worth it. It’s one of those fun Chicago things to do that both locals and visitors adore.

5. Visit the Chicago History Museum

To truly appreciate the legacy of Chicago, a trip to the Chicago History Museum in Lincoln Park is a must. The museum features engaging exhibits, including artifacts from the Great Chicago Fire and interactive displays about the Underground Railroad. You’ll learn about the diverse communities that shaped Chicago into the vibrant city it is today.

The museum not only preserves history but also instills pride in the achievements and struggles of its residents. Friendly staff and volunteers often lead tours that provide even deeper insights into the artifacts and stories on display.

6. Experience the Magnificent Mile Nightlife

The Magnificent Mile is not just a shopper’s paradise; it transforms into a lively scene after sunset. Upscale rooftop bars like The Signature Lounge at the John Hancock Center offer cocktails with stunning views. On the flip side, local hotspots like The Wieners Circle serve up memorable experiences with late-night festivities and their famous Chicago-style hot dogs.

Don’t miss out on this lively nightlife scene where laughter, music, and the bustling atmosphere create an unforgettable experience.

7. Discover Local Brews in the West Loop

The West Loop has earned its reputation as a gourmet destination, but it’s also home to a thriving craft beer scene. An annual event worth attending is “Beerhoptacular,” which showcases local breweries like Half Acre and Goose Island. You’ll get a taste of the city’s best brews while mingling with fellow beer aficionados.

Plus, taking a brewery tour offers an up-close glimpse into the brewing process. You’ll not only sample various types of craft beers but also gain insights from passionate brewers eager to share their craft with you.

Unforgettable Experiences Beyond Chicago

If you find yourself with some extra time, consider venturing out to explore nearby cities, each rich in culture and unique attractions.

Things to Do in Knoxville, TN

Knoxville is a vibrant city filled with impressive experiences. Don’t miss the Knoxville Museum of Art, which highlights local artists and hosts exciting community events. The Old City district buzzes with eclectic shops, restaurants, and nightlife, making it a perfect spot to unwind after a day of exploration. For more information, kickstart your research with these things to do in Knoxville.

Things to Do in Richmond, VA

Richmond keeps history alive through destinations like the Virginia State Capitol and the Civil War Museum. Be sure to stroll along Monument Avenue to admire its historical plaques and statues. Treat your taste buds at local restaurants like The Roosevelt, where you can dive into a rich blend of Southern cuisines. If you’re curious about other adventures, check out the things to do in Richmond, VA for more experiences.

Things to Do in Chattanooga , TN

Chattanooga, known for its breathtaking scenery, has much to offer to outdoor enthusiasts and casual visitors alike. A trip to the Tennessee Aquarium, the largest freshwater aquarium in the world, is a must-do. Take in scenic views at Lookout Mountain, where you can try out the suspended glass walkway if you’re feeling adventurous. Don’t forget to explore more about the city through local resources for fun things to do in Chattanooga.

Things to Do in Savannah, GA

Savannah’s Historic District is a slice of tranquility, featuring cobblestone streets and lush public squares. Explore the whimsical Bonaventure Cemetery, known for its hauntingly beautiful landscapes. Also, River Street is a delightful stop for local shops and eateries offering the best in Southern delicacies. If you’re heading south, look into things to do in Savannah, GA for a memorable experience.

In 2026, Chicago remains a treasure trove of experiences that effortlessly blend rich history with modern flair. From the arts to culinary delights, the Windy City has something for everyone. So get out there and dive into all the astonishing things Chicago has to offer today!

Things to Do Chicago That Will Amaze You Today

Hidden Gems and Fun Facts

When exploring the things to do Chicago has to offer, you might stumble upon some quirky surprises! For instance, did you know Chicago hosts pop-up events and festivals celebrating everything from food trucks to art installations? This city is a melting pot of culture, and speaking of culture, you can find delicacies here that you won’t find anywhere else—like the unique taste of pork floss! This cozy little treasure of a dish has stolen the hearts of many food lovers. And while you’re tasting your way through the city, thinking about more exciting vibes? Be sure to check out the buzzing spot for good fish And chicken that locals rave about!

Architectural Wonders

As you walk along the breathtaking skyline, take a moment to appreciate the mix of architecture that defines the city. Did you know Chicago is home to the world’s tallest building, the Willis Tower? While you’re up there, try to imagine the thrill of looking down from the Skydeck. It’s an experience akin to visiting Avalon, California, but in a bustling urban setting! This architectural journey doesn’t just stop at skyscrapers; the history behind Chicago’s buildings showcases a fascinating tale of resilience during the Great Fire. Those stories add an extraordinary depth to your exploration, making each tour worthwhile!

Artistic Adventures and Local Vibes

Art is another specialty of the things to do Chicago scene. The city boasts an impressive array of galleries and public art installations that can dazzle anyone. One intriguing encounter to catch is the city’s famous murals—you may even find one that pays homage to Albus Dumbledore! And for those who enjoy some fun under the sun, be sure to hop over to the Chicago Riverwalk, where live music and food festivals keep the energy buzzing. If you’re looking for other Miams in the U.S., you can also explore this passionate city and find a variety of events that ignite that same fiery spirit you experience in things to do Miami.

Incorporating these elements into your trip transforms your ordinary day into an unforgettable experience. So, grab your friends or family and dive into these diverse offerings, making memories that’ll last a lifetime through the fantastic things to do Chicago has waiting just for you!