With its world-class museums, acclaimed dining scene, iconic sports teams, and lively entertainment options, Chicago offers endless fun things to do for visitors. As a traveler to the Windy City, you’ll find a variety of attractions to fill your itinerary. Here are 10 Free things to do in Chicago and sights to make the most of your Chicago trip.
List Of 10 Fun Things To Do In Chicago
1. Millennium Park
Start your Chicago adventure at Millennium Park, one of the most popular free things to do in Chicago. Located downtown, this sprawling urban park features stunning contemporary architecture and art installations. Snap photos in front of Cloud Gate, the mirrored stainless steel sculpture nicknamed “The Bean” for its unique shape. From May to September, relax on the grass while enjoying free concerts at the Frank Gehry-designed Jay Pritzker Pavilion. With so much to see and do, Millennium Park is easily one of the top fun things to do in Chicago.
2. Chicago’s Architectural Marvels from the Chicago River
Next, experience Chicago’s impressive architecture from the Chicago River. Taking an architecture boat tour is one of the best things to do in Chicago to see the city’s iconic skyscrapers and learn about notable buildings. As you cruise down the river, your guide will point out famous structures like the Willis Tower, Tribune Tower, Marina City, and more. You’ll gain insight into Chicago’s history and admire the city from unique vantage points.
3. Navy Pier
No trip to Chicago is complete without visiting Navy Pier, the city’s bustling lakefront playground. Strolling down the half-mile pier is one of the most fun things to do in Chicago on any itinerary. Grab food from the various eateries, ride the iconic Centennial Wheel for panoramic views, or catch a performance at the Chicago Shakespeare Theater. You can easily spend hours exploring the endless shops, restaurants, and attractions. Navy Pier offers the perfect mix of sightseeing, dining, and entertainment.
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4. Chicago Cubs
Of course, you can’t talk about Chicago without discussing its beloved baseball team, the Chicago Cubs. Catching a game at the historic Wrigley Field is a quintessential thing to do in Chicago. Cheer on the Cubbies as you take in the vintage ballpark, soak up the energetic atmosphere, and indulge in Chicago staples like hot dogs and popcorn. If you time your visit right, you may even get to see the Cubs play their longtime rivals, the St. Louis Cardinals.
5. Art Institute of Chicago
For art lovers, the Art Institute of Chicago is a must-visit attraction. Housing over 300,000 works, it’s one of the oldest and largest art museums in the country. See iconic pieces like Edward Hopper’s Nighthawks and Grant Wood’s American Gothic up close. Wander the collection galleries and be sure to stop at the museum’s unique Tiffany glass dome. No Chicago bucket list is complete without seeing the Art Institute’s world-renowned collection.
6. Willis Tower and its Skydec
Of course, you can’t mention Chicago attractions without including Willis Tower and its Skydeck. Gaining fame as the world’s tallest building for over two decades, Willis Tower’s Observation Deck offers breathtaking city views from over 1300 feet up on the 103rd floor. The glass balconies even let you step out over the ledge, making it one of the most thrilling things to do in Chicago. On clear days, you can see four states from the top!
7. John Hancock Center
While you’re checking sky-high attractions off your Chicago list, make time to visit 360 Chicago, the observatory at the John Hancock Center. In addition to panoramic views, this 94th-floor observatory provides interactive exhibits and displays with details on Chicago’s history, culture, sports, and more. Their open-air skywalk offers a unique vantage point, 1,000 feet up in the sky. It’s one of the most fun things to do in Chicago for stellar city views.
8. Enjoy Chicago-style pizza
You can’t leave Chicago without trying the city’s famous deep-dish pizza. For an authentic deep dish, make a stop at Lou Malnati’s Pizzeria, a local favorite since 1971. Their buttery crust, mounds of mozzarella, chunky tomato sauce, and secret spice mix create a mouthwatering deep-dish experience. It’s an absolute must-do foodie activity and one of the top things to do in Chicago for couples looking for a casual, tasty night out.
Another excellent way to taste Chicago’s cuisine is through a dedicated food tour. Chicago Food Planet offers 2-3 hour walking tours that hit the city’s top tastes. From deep-dish pizza to Italian beef sandwiches, you’ll get a delicious bite of Chicago’s diverse neighborhoods. It’s easily one of the best things to do in Chicago for food lovers.
9. Visit the Second City
When it’s time for a laugh, head to “The Second City Comedy Club”, a Chicago staple since 1959. Grab a drink and appetizer while watching an incredible improv or sketch comedy show. Countless Saturday Night Live legends like Tina Fey, Stephen Colbert, and Bill Murray got their start on Second City’s stages. Catching a live show here is undoubtedly one of the most entertaining things to do in Chicago at night.
10. Explore parks and Cultural Delights
Finally, make time to explore Chicago’s sprawling public parks and green spaces. Take a stroll down the iconic Magnificent Mile, especially during the holidays when it sparkles with lights and decorations. Lincoln Park, Grant Park, and Maggie Daley Park offer places to picnic, paths for walking or biking, and free cultural programming. Chicago’s parks host some of the best free things to do in Chicago.
