If you're looking for fun things to do in Chicago, you're in for a real treat. The Windy City is packed with activities that mix excitement, culture, and a bit of that classic Chicago charm. Whether you're a local or just visiting, there’s always something new to uncover around every corner.

From iconic landmarks to hidden gems, Chicago offers a wide range of experiences that’ll keep you coming back for more. You can start your day strolling along the lakefront, then catch a Bulls game in the evening, and still have time for an escape room or two in between.

What makes this city so special is how it blends the old with the new, the expected with the unexpected. So whether you're into history, food, art, or just looking for something a little unusual, Chicago’s got you covered.

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Table of Contents

• Explore the Lakefront and Scenic Walks
• Dive Into Chicago’s World-Class Museums
• Savor the Flavors of Chicago
• Check Out Hidden Attractions and Unique Spots
• Experience Chicago’s Vibrant Nightlife
• Catch a Live Sports Game
• Frequently Asked Questions

Explore the Lakefront and Scenic Walks

One of the most popular and free things to do in Chicago is walking or biking along the lakefront. The city’s shoreline offers some of the best views and fresh air you can find without ever leaving the downtown area.

The 18-mile Lakefront Trail stretches from the southern neighborhoods all the way up to the north side, passing parks, beaches, and skyline views along the way. It’s a favorite for joggers, cyclists, and even dog walkers.

Grant Park is another must-see spot, home to the famous Buckingham Fountain. You can relax on the grass, snap some photos of the skyline, or stop by during one of the many festivals held there throughout the year.

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Want a view from above? The 360 Chicago Observation Deck in the John Hancock Center offers a thrilling way to take in the city. The Skywalk Overlook lets you stand on a glass platform 1,000 feet in the air. It’s definitely not for the faint of heart, but totally worth the adrenaline rush.

Dive Into Chicago’s World-Class Museums

Chicago is home to some of the most respected museums in the world. Whether you're into art, science, or history, you’ll find a place that speaks to your interests.

The Art Institute of Chicago is a top spot for art lovers. It houses everything from ancient artifacts to modern masterpieces. The museum’s collection includes pieces by famous artists like Van Gogh, Monet, and Grant Wood.

Kids and adults alike enjoy the Museum of Science and Industry, especially the interactive exhibits and the U-505 submarine display. It’s a place where learning feels more like playing.

For something different, the Chicago History Museum offers a deep dive into the city’s past, including the Great Chicago Fire and the World’s Fair.

So if you're into culture, a day spent hopping from one museum to another is one of the most fun things to do in Chicago.

Savor the Flavors of Chicago

Let’s talk food—because no trip to Chicago is complete without trying the local cuisine. Deep-dish pizza is a must, and you’ll find plenty of places claiming to have the best slice in town.

Giordano’s, Lou Malnati’s, and Pequod’s all offer their own unique twists on this cheesy, thick-crusted classic. So grab a group of friends and order a pie to share—it’s a filling experience, to say the least.

Don’t forget to try a Chicago-style hot dog, too. Loaded with mustard, relish, onions, tomatoes, sport peppers, a pickle spear, and a dash of celery salt—all on a poppy seed bun—it’s a flavor explosion you won’t find anywhere else.

If you're feeling adventurous, stop by Portillo’s or any neighborhood stand for a real taste of local food culture. And for dessert? Get a Maxwell Street Polish with an Italian beef sandwich on the side. It’s messy, it’s delicious, and it’s all Chicago.

Check Out Hidden Attractions and Unique Spots

While Chicago’s big-name attractions are great, the city also has a ton of lesser-known spots that are just as fun—and sometimes even more memorable.

For a quirky and unusual experience, head to Merz Apothecary in Lincoln Park. It’s more than just a store—it’s a step back in time. The shop has been around since the 1800s and is filled with vintage bottles, old-world charm, and a curated selection of wellness products.

Looking for something a little spooky? The Medieval Torture Museum in Old Town is not for the faint of heart. It showcases all kinds of ancient torture devices and offers a dark but fascinating look at history. It’s definitely one of those weird-but-cool things to do in Chicago.

Another hidden gem is Oz Park, a small but charming park near Lincoln Park. As the name suggests, it’s themed around *The Wizard of Oz* with statues of Dorothy, Toto, the Cowardly Lion, and friends. It’s a peaceful spot to relax and snap a few photos, especially during the fall when the leaves are changing.

Experience Chicago’s Vibrant Nightlife

Chicago comes alive at night, offering everything from jazz clubs to rooftop bars with skyline views. Whether you're looking for a quiet drink or a night of dancing, there’s something for every kind of night owl.

If you’re into live music, you can’t miss the legendary jazz clubs like the Green Mill or Jazz Showcase. These spots have hosted some of the best musicians in history and still offer a rich, intimate experience today.

For skyline views and a more modern vibe, head up to the Signature Lounge at the 96th floor of the John Hancock Building. The drinks are great, but the views are even better—especially at sunset.

And if you’re looking to dance the night away, the city’s clubs like Sound and Spybar are always buzzing with energy and great music. Just be sure to dress the part and check out the dress code ahead of time.

So if you’re wondering what to do after dark, Chicago’s nightlife scene is definitely one of the fun things to do in Chicago that shouldn’t be missed.

Catch a Live Sports Game

Sports fans, this one’s for you. Chicago is a city that lives and breathes sports, and catching a live game is one of the most exciting things you can do here.

Whether it’s a Bulls basketball game at the United Center, a Cubs or White Sox baseball game, or a Bears football match (though those are a bit further out), the energy in the stadiums is something special.

Even if you’re not a die-hard fan, the atmosphere alone makes it worth checking out. There’s nothing quite like the roar of the crowd or the feeling of being part of something bigger when your team wins.

And if you’re visiting in the summer, Wrigley Field is a must. Watching a game at this historic ballpark, with ivy-covered walls and classic charm, feels like stepping into a piece of baseball history.

So grab a hot dog, join the chants, and let yourself get swept up in the excitement of Chicago sports.

Frequently Asked Questions

What is the #1 attraction in Chicago?

The number one attraction in Chicago is often considered to be Navy Pier. With its Ferris wheel, restaurants, shops, and seasonal fireworks, it’s a top spot for both tourists and locals looking for fun things to do in Chicago.

What are some unusual things to do in Chicago?

From visiting the Medieval Torture Museum to exploring Merz Apothecary or hanging out in Oz Park, Chicago has plenty of quirky and unusual things to do. These spots offer a different kind of experience beyond the usual tourist stops.

Are there free things to do in Chicago?

Absolutely! You can walk along the lakefront, visit free museum days, explore neighborhood parks, or enjoy free concerts and events in the summer. Chicago offers many ways to enjoy the city without breaking the bank.

For more ideas, you can learn more about fun things to do in Chicago on our site, where we break down the best activities for every type of traveler.