With its iconic skyline, deep-dish pizza, and vibrant culture, Chicago is one of America’s most exciting cities. Whether you’re into art, food, music, sports, or just soaking in the city vibe, the Windy City has something for every kind of traveler.
Whether you’re visiting for a weekend or you’re a local looking for inspiration, here’s a fresh list of fun things to do in Chicago that you’ll absolutely love.
🏙️ 1. Take in the Skyline from Sky-deck Chicago
Located on the 103rd floor of the Willis Tower (formerly Sears Tower), the Skydeck offers jaw-dropping views of the city and beyond. Step onto The Ledge—a glass balcony extending 4 feet outside the building—for a photo you won’t forget.
🧀 2. Try Authentic Chicago Deep-Dish Pizza
A visit to Chicago isn’t complete without digging into a deep-dish pizza. Head to local legends like Giordano’s, Lou Malnati’s, or Pequod’s for cheesy, saucy deliciousness you’ll be dreaming about long after your trip.
🖼️ 3. Explore the Art Institute of Chicago
Home to Monet, Van Gogh, Picasso, and American classics like “American Gothic,” this world-class museum is a haven for art lovers. The Art Institute also has a stunning modern wing and beautiful gardens.
🛶 4. Kayak on the Chicago River
Yes, kayaking in the middle of a city is a thing—and it’s amazing! Paddle past skyscrapers along the Chicago River for a totally unique perspective. Sunset and architecture-themed tours are especially popular.
🏞️ 5. Stroll Through Millennium Park
Snap a selfie at the Cloud Gate (aka “The Bean”), enjoy free concerts at Jay Pritzker Pavilion, and relax by the Crown Fountain. This urban park in the heart of downtown is always buzzing with activity.
🌿 6. Visit Lincoln Park Zoo (It’s Free!)
One of the oldest zoos in the country—and completely free!—Lincoln Park Zoo is home to gorillas, penguins, lions, and more. It’s a great place to explore with kids or simply enjoy a peaceful afternoon.
🎡 7. Ride the Centennial Wheel at Navy Pier
Navy Pier is a family-friendly destination packed with attractions, but the Centennial Wheel is the star. The enclosed, climate-controlled gondolas offer stunning views of Lake Michigan and the city skyline.
🚲 8. Bike or Walk the Lakefront Trail
Stretching 18 miles along Lake Michigan, the Lakefront Trail is perfect for biking, jogging, or taking a leisurely walk. You’ll pass beaches, parks, museums, and even the Shedd Aquarium along the way.
🍻 9. Go on a Chicago Brewery Tour
Chicago has a thriving craft beer scene. Visit breweries like Revolution Brewing, Half Acre, or Lagunitas to sample local flavors and take a tour of their brewing process.
🏛️ 10. Dive into Science at the Museum of Science and Industry
With interactive exhibits, a WWII submarine, a working coal mine, and a mirror maze, this museum is anything but boring. It’s one of the most fun and educational places to visit in Chicago.
🎭 11. Catch a Show at The Second City
Want to laugh till your cheeks hurt? Head to The Second City, the legendary comedy club where greats like Tina Fey, Steve Carell, and Bill Murray got their start.
🎶 12. Experience Chicago’s Music Scene
From jazz and blues to indie rock, Chicago’s music scene is electric. Visit historic venues like The Green Mill, House of Blues, or Thalia Hall to experience live performances from up-and-coming and legendary artists.
🛍️ 13. Shop the Magnificent Mile
Stretching down Michigan Avenue, the Magnificent Mile is a shopper’s paradise. Explore flagship stores, high-end boutiques, and designer brands. Don’t forget to stop at The Water Tower Place for a mix of shopping and dining.
Explore Best Indian Restaurants in Chicago
🌇 Final Thoughts
From sky-high views to river adventures, world-class museums to comedy shows, Chicago is a city that knows how to have fun. Whether you’re into food, art, nature, or nightlife, the Windy City welcomes you with open arms and endless things to explore.
So pack your jacket (because it’s windy for a reason), bring your appetite, and get ready to fall in love with Chicago.
Frequently Asked Questions (FAQs)
A: Millennium Park, especially The Bean (Cloud Gate), is one of the most visited and photographed attractions in Chicago.
A: Chicago is world-famous for its deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, and Garrett Popcorn.
A: Yes! Some of the best free attractions include Lincoln Park Zoo, Millennium Park, Navy Pier (entry), and many lakefront beaches and trails.
A: Kayaking on the Chicago River, visiting The Second City comedy club, and exploring the underground Pedway system offer truly local and memorable experiences.
A: The best time is late spring (May–June) or early fall (September–October), when the weather is mild and outdoor activities are in full swing.