The 10 Best Things To Do In Chicago

Ah, Chicago – the Windy City! It’s a place where the skyscrapers reach for the clouds and the deep-dish pizza is as hearty as the city’s history. If you’re planning a trip to this bustling metropolis, you’re in for a treat. There’s a smorgasbord of activities that can fill your itinerary faster than you can say “Al Capone.” Let’s dive into the top 10 things that should be on your must-do list when you visit Chicago.

1. Get Sky-High at Willis Tower Skydeck

First up, let’s talk about touching the sky. The Willis Tower, formerly known as the Sears Tower, is not just any old skyscraper. It’s an icon. Step onto the Skydeck and the Ledge, a glass box that extends out from the 103rd floor, and you’ll feel like you’re floating. The view? Simply breathtaking. You can see four states on a clear day!

2. Stroll Through Millennium Park

Millennium Park is the heart of Chicago’s outdoor spaces. It’s where art, community, and nature intertwine. Snap a selfie with the reflective glory of Cloud Gate, affectionately known as “The Bean.” In the summer, the park’s alive with concerts and food festivals. In the winter, lace up your skates for a whirl around the ice rink.

3. Explore the Art Institute of Chicago

Art lovers, rejoice! The Art Institute of Chicago is a treasure trove of masterpieces. From Monet’s serene water lilies to the bold strokes of Van Gogh’s self-portrait, it’s a feast for the senses. Don’t miss the Thorne Miniature Rooms – they’re a quirky collection of tiny, detailed interiors that are sure to captivate.

4. Take a Chicago Riverwalk and Architecture Cruise

Chicago’s architecture is world-renowned, and there’s no better way to see it than from the river. Hop on a boat and cruise along the Chicago River. You’ll be regaled with stories of the city’s architectural marvels and the ambitious people who built them. It’s a must-do for history buffs and photography enthusiasts alike.

5. Catch a Game at Wrigley Field

Even if you’re not a baseball fan, Wrigley Field is a slice of pure Americana. It’s one of the oldest ballparks in the country and oozes charm. Grab a hot dog, sing “Take Me Out to the Ball Game,” and soak in the electric atmosphere. If the Cubs aren’t in town, take a tour and learn about the legendary “Curse of the Billy Goat.”

6. Visit the Museum of Science and Industry

Ready for a mind-blowing experience? The Museum of Science and Industry is where you can explore a World War Ii submarine, experience a simulated tornado, and even descend into a Coal mine. It’s interactive, educational, and fun for all ages. Trust me, you’ll leave with a sense of wonder.

7. Enjoy the Views from 360 CHICAGO Observation Deck

For another sky-high adventure, head to 360 CHICAGO. Located on the 94th floor of the John Hancock Center, it offers panoramic views of the city and Lake Michigan. If you’re feeling daring, try TILT – a glass platform that tilts you out over the city. It’s an adrenaline rush with a view!

8. Indulge in Chicago’s Food Scene

Chicago’s food scene is legendary. From the aforementioned deep-dish pizza to the classic Chicago-style hot dog (no ketchup, please!), your taste buds are in for a treat. Don’t forget to try an Italian beef Sandwich, another local favorite. And for dessert? A slice of Eli’s famous cheesecake is a sweet ending to any meal.

9. Take a Walk on The Magnificent Mile

Shopaholics, welcome to paradise. The Magnificent Mile is Chicago’s premier commercial district, boasting an array of shops, boutiques, and department stores. Even if shopping isn’t your thing, the vibrant atmosphere and historic buildings make for a great stroll.

10. Unwind at the Lincoln Park Zoo

Last but not least, the Lincoln Park Zoo is a peaceful escape from the city buzz. It’s one of the oldest zoos in the country and, best of all, it’s free! See everything from majestic lions to playful penguins. It’s a delightful way to spend an afternoon, especially if you’re traveling with kids.


  • What’s the best time of year to visit Chicago?

    Summer and fall are fantastic, with numerous festivals and pleasant weather. Winters can be harsh, but the city’s beauty under a blanket of snow is undeniable.

  • Is the Chicago CityPASS worth it?

    If you’re planning to hit several of the attractions listed here, absolutely. It can save you time and money on admission fees.

  • Can I get around Chicago without a car?

    Definitely. The ‘L’ train and buses are efficient, and many attractions are within walking distance in the downtown area.


Chicago is a city that’s rich in culture, history, and culinary delights. From the dizzying heights of its observation decks to the cozy corners of its world-class museums, there’s something for everyone. Whether you’re cheering on the Cubs at Wrigley Field, marveling at the city’s architectural wonders, or indulging in a slice of deep-dish pizza, your time in Chicago is sure to be unforgettable. So pack your bags, grab your camera, and get ready for an adventure in the city that feels like home, no matter where you’re from.

Remember, this list is just the tip of the iceberg. Chicago’s charm lies in its ability to surprise you at every corner. So go ahead, explore, and let the Windy City sweep you off your feet!

Kurby Team

The Kurby Content Team is a diverse group of seasoned real estate experts dedicated to providing insightful, reliable information for homebuyers, real estate investors, and real estate agents. With backgrounds ranging from real estate brokerage, property investment, and residential home buying, our team combines decades of experience with a passion for demystifying the real estate world. We at Kurby are committed to helping you make informed, successful real estate decisions. Whether you're a first-time homebuyer, a seasoned investor, or a real estate professional, count on the Kurby Content Team to deliver the most relevant, actionable real estate content you need.