Chicago — often called the “Windy City” — is a vibrant metropolis that offers a rich blend of culture, history, architecture, food, and fun.
Nestled on the shores of Lake Michigan, it’s a city of striking skylines, legendary deep-dish pizza, and passionate sports fans.
Whether you’re a first-time visitor or a lifelong Chicagoan rediscovering your hometown, the city never fails to inspire.
From sky-high observatories and world-renowned museums to stunning lakefront parks and neighborhood gems, this guide uncovers 17 of the best things to do in Chicago.
Whether you’re here for a weekend or a long stay, these experiences will help you make the most of your trip.
1. Marvel at the Skyline from Skydeck Chicago
Located in the Willis Tower (formerly Sears Tower), the Skydeck is a bucket-list stop. Step onto The Ledge, a glass balcony extending 1,353 feet over the city, for an unforgettable view of Chicago and even neighboring states on a clear day.
2. Stroll Through Millennium Park & See “The Bean”
Millennium Park is one of Chicago’s most photographed destinations. At its heart is Cloud Gate, affectionately known as “The Bean,” a giant reflective sculpture that captures the city skyline like no other. Don’t miss the Crown Fountain or Jay Pritzker Pavilion nearby.
3. Explore the Art Institute of Chicago
This world-class museum is home to iconic pieces such as Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and works by Monet, Van Gogh, and Picasso. It’s a must for art lovers and consistently ranks among the best museums in the world.
4. Take an Architecture River Cruise
Chicago’s skyline is legendary, and there’s no better way to admire it than from the Chicago River. Guided boat tours give insight into the city’s architectural history and offer some of the most Instagram-worthy views.
5. Enjoy the Views from 360 Chicago (John Hancock Building)
Another sky-high experience, 360 Chicago features Tilt — a glass-enclosed platform that tilts you outward over the Magnificent Mile. The views of Lake Michigan and the cityscape are breathtaking, especially at sunset.
6. Walk or Bike the Lakefront Trail
Spanning 18 miles, the Lakefront Trail offers a scenic route for walking, jogging, or biking with incredible views of Lake Michigan. It connects many of Chicago’s top attractions, beaches, and parks.
7. Visit Navy Pier
This bustling entertainment hub features:
- A Ferris wheel with lake and skyline views
- The Chicago Children’s Museum
- Seasonal fireworks
- Boat tours and dinner cruises
- Shopping, restaurants, and public art
Great for families, couples, and solo travelers alike.
8. Explore the Field Museum of Natural History
Home to Sue the T. rex, one of the most complete Tyrannosaurus rex skeletons ever discovered, the Field Museum offers immersive exhibits on ancient civilizations, geology, biology, and anthropology.
9. Step into the Past at the Museum of Science and Industry
This massive, hands-on museum is a favorite among both kids and adults. Highlights include:
- A real German U-505 submarine
- A replica coal mine
- A futuristic Smart Home
- Science Storms and weather simulations
10. Taste Chicago’s Iconic Foods
No trip is complete without indulging in:
- Deep-dish pizza (try Lou Malnati’s or Giordano’s)
- Chicago-style hot dogs (sans ketchup!)
- Italian beef sandwiches
- Garrett’s Popcorn
- Ethnic cuisine from neighborhoods like Pilsen (Mexican), Chinatown, and Little Italy
11. Relax in Lincoln Park & Visit the Zoo
Lincoln Park is Chicago’s largest public park, offering gardens, ponds, trails, and free entry to the Lincoln Park Zoo, one of the oldest zoos in the country. The park also houses the Peggy Notebaert Nature Museum and Chicago History Museum.
12. Discover Neighborhood Charm in Wicker Park & Logan Square
Beyond downtown, Chicago’s neighborhoods are full of personality. Wicker Park and Logan Square are known for:
- Trendy boutiques and record shops
- Independent coffee shops
- Murals and street art
- A lively nightlife scene
13. Explore the Shedd Aquarium
With more than 32,000 animals, Shedd Aquarium offers a glimpse into aquatic life from around the world. Popular exhibits include Amazon Rising, Wild Reef, and Caribbean Reef — perfect for a family day out.
14. Catch a Game at Wrigley Field
Home to the Chicago Cubs, Wrigley Field is a legendary ballpark that dates back to 1914. Whether or not you’re a baseball fan, the atmosphere is electric. You can even tour the stadium on non-game days.
15. Take a Street Art Walking Tour
Chicago is a canvas for urban art. Head to neighborhoods like Pilsen, Wicker Park, or Logan Square for murals, graffiti walls, and local art installations that tell stories about the city’s diverse cultural landscape.
16. Attend a Comedy Show at The Second City
Chicago is the birthplace of improv comedy, and The Second City has produced legends like Tina Fey, Bill Murray, and Steve Carell. Catch a live show to laugh the night away and support up-and-coming talent.
17. Relax at a Beach Along Lake Michigan
Yes, Chicago has beaches! During summer, the lakefront comes alive with locals and tourists sunbathing, swimming, and playing volleyball. Check out:
- North Avenue Beach
- Oak Street Beach
- Montrose Beach (dog-friendly!)
- 31st Street Beach (great views)
Bonus Tips for Visiting Chicago
- Transportation: Use the “L” trains and buses with a Ventra card for affordable, fast transit.
- Best Time to Visit: Spring (May–June) and Fall (September–October) offer pleasant weather and fewer crowds.
- CityPASS: For longer stays, consider the Chicago CityPASS for discounted entry to major attractions.
- Free Attractions: Many museums offer free admission days for Illinois residents.
Conclusion
Whether you’re marveling at skyscrapers, diving into world-class museums, savoring iconic eats, or wandering through eclectic neighborhoods, Chicago has something for every type of traveler.
With its unique blend of Midwestern charm and big-city energy, the Windy City delivers unforgettable experiences.
From arts and architecture to sports and lakeside relaxation, this guide to the 17 best things to do in Chicago will help you plan a trip that’s rich in memories, adventure, and local flavor.
