Chicago, Illinois, is a city that’s got it all—stunning architecture, world-class food, and a vibe that’s equal parts laid-back and electric.
Whether you’re a first-time visitor or a seasoned traveler, the Windy City never fails to impress.
From iconic landmarks to hidden gems, Chicago is packed with experiences that’ll make you want to extend your trip.
So, buckle up, because we’re about to dive into the 12 best things to do in Chicago that’ll have you planning your next visit before you’ve even left.
Ready to explore? Let’s get into it. Whether you’re strolling along the lakefront, digging into a deep-dish pizza, or catching a game at Wrigley Field, Chicago has something for everyone.
And trust me, by the end of this list, you’ll be itching to book your ticket. Let’s make your Chicago adventure unforgettable!
1. Marvel at the Skyline from Willis Tower Skydeck
If you’re visiting Chicago, you can’t miss the Willis Tower Skydeck. Standing at 1,450 feet, it’s one of the tallest buildings in the Western Hemisphere.
The Skydeck offers breathtaking views of the city, Lake Michigan, and even four neighboring states on a clear day.
But the real thrill? Stepping onto The Ledge, a glass balcony that extends four feet outside the building.
It’s not for the faint of heart, but it’s a must-do for anyone looking to experience Chicago from above. Pro tip: Visit during sunset for a view that’ll leave you speechless.
2. Stroll Through Millennium Park and “The Bean”
No trip to Chicago is complete without a visit to Millennium Park, home to the iconic Cloud Gate sculpture (aka “The Bean”).
This shiny, reflective masterpiece is perfect for snapping selfies and capturing the city’s skyline in its curves.
The park itself is a hub of activity, with free concerts, art installations, and lush gardens.
In the summer, grab a blanket and relax at the Jay Pritzker Pavilion, an outdoor concert venue that hosts everything from jazz to classical music.
3. Explore the Art Institute of Chicago
Art lovers, rejoice! The Art Institute of Chicago is one of the oldest and largest art museums in the U.S., and it’s a treasure trove of masterpieces.
From Grant Wood’s American Gothic to Georges Seurat’s A Sunday on La Grande Jatte, the collection is mind-blowing.
The museum also features stunning architecture and rotating exhibits, so there’s always something new to discover. Don’t rush—this place deserves a full afternoon.
4. Catch a Game at Wrigley Field
Even if you’re not a baseball fan, catching a game at Wrigley Field is a quintessential Chicago experience.
The historic ballpark, home to the Chicago Cubs, has been around since 1914 and oozes old-school charm.
Grab a hot dog, sing “Take Me Out to the Ball Game” during the seventh-inning stretch, and soak in the electric atmosphere. Whether the Cubs win or lose, you’ll leave with a newfound love for America’s favorite pastime.
5. Walk Along the Chicago Riverwalk
The Chicago Riverwalk is the city’s crown jewel, offering a scenic stroll along the Chicago River.
Lined with restaurants, bars, and public art, it’s the perfect spot to unwind and take in the city’s architectural beauty.
For a unique perspective, hop on an architecture boat tour and learn about the skyscrapers that make Chicago’s skyline so iconic.
Trust me, you’ll gain a whole new appreciation for the city’s design.
6. Dig Into Chicago’s Famous Deep-Dish Pizza
Let’s be real—you can’t visit Chicago without trying its legendary deep-dish pizza. This isn’t your average slice; it’s a thick, cheesy, saucy masterpiece that’s practically a meal in itself.
Head to iconic spots like Lou Malnati’s or Giordano’s to taste the real deal. Whether you’re a meat lover or prefer a veggie-loaded pie, there’s a deep-dish pizza in Chicago with your name on it.
7. Discover Navy Pier’s Fun and Festivities
Navy Pier is Chicago’s playground, offering something for everyone. Take a ride on the Ferris wheel for stunning views of the lakefront, catch a show at the Chicago Shakespeare Theater, or simply enjoy a leisurely stroll along the pier.
In the summer, the pier comes alive with fireworks, live music, and outdoor dining. It’s a great spot to unwind and soak in the city’s vibrant energy.
8. Immerse Yourself in Science at the Museum of Science and Industry
The Museum of Science and Industry is a hands-on wonderland that’s fun for all ages. From exploring a real U-505 submarine to walking through a replica coal mine, the exhibits are both educational and entertaining.
Don’t miss the Science Storms exhibit, where you can witness tornadoes and avalanches up close. It’s a perfect rainy-day activity that’ll leave you in awe.
9. Shop ‘Til You Drop on the Magnificent Mile
Calling all shopaholics! The Magnificent Mile is Chicago’s premier shopping destination, featuring everything from luxury boutiques to flagship stores.
Even if shopping isn’t your thing, the area is worth a visit for its stunning architecture and lively atmosphere.
Stop by the Historic Water Tower, one of the few buildings that survived the Great Chicago Fire, and snap a pic for the ‘Gram.
10. Relax at Lincoln Park Zoo
Did you know the Lincoln Park Zoo is one of the oldest zoos in the U.S. and completely free? That’s right—you can spend the day admiring lions, giraffes, and penguins without spending a dime.
The zoo also features beautiful gardens and a farm-in-the-zoo exhibit, making it a great spot for families or anyone looking to connect with nature.
11. Take in the Views at 360 Chicago
For another sky-high perspective, head to 360 Chicago at the John Hancock Center.
Located 1,000 feet above the city, this observation deck offers panoramic views and a thrilling tilt feature that leans you out over the city.
It’s a bit less crowded than the Willis Tower, so you can enjoy the views without the hustle and bustle.
12. Explore the Vibrant Neighborhoods
Chicago’s neighborhoods are as diverse as they are dynamic. From the artsy vibes of Wicker Park to the cultural richness of Pilsen, each area has its own unique flavor.
Take a walking tour, sample local eats, and chat with residents to get a true sense of what makes Chicago so special.
Conclusion
Chicago is a city that never disappoints, offering a mix of iconic landmarks, cultural experiences, and hidden gems.
Whether you’re marveling at the skyline, indulging in deep-dish pizza, or exploring vibrant neighborhoods, there’s always something new to discover.
So, what are you waiting for? Start planning your trip to Chicago today and experience the 12 best things to do in Chicago for yourself. Trust me, you won’t regret it!