9 Adventurous Things To Do in Chicago

Chicago, otherwise known as the Windy City, Chi-town, or the Second City, is home to many adventurous and exhilarating things to do. If you are a thrill seeker, or even if you just want to feel your adrenaline pumping, there are a variety of activities for you to experience in Chicago, from lower key adventures like playing sports to more breathtaking experiences like viewing the city from the tops of some of Chicago’s tallest buildings. Whatever your preference is, there is something for everyone seeking a thrilling time in Chicago. We’ve compiled a list of 9 adventurous things to do in Chicago to help you decide which activity is best for you.

Take a Segway tour

If you want to explore the city in a unique way, and save yourself from sore feet at the same time, then you might want to consider taking a Segway tour. Gliding around on Segways is an easy way to view the city, and is ideal for both beginners and experienced riders. There are many different tours you can go on that take you past iconic landmarks and architectural features around the city. Plus, you’ll be able to feel the wind in your face as you glide around the city!

Attend a music festival

Chicago has many exciting music festivals that take place on neighborhood streets and downtown parks. One upcoming music festival is Pitchfork, from September 10th to the 12th at Union Park. The Pitchfork Music Festival usually garners 50,000 attendees and draws performers from genres like alternative rock, rap and hip-hop, electronica, and hardcore punk. If you like electronic music, then you’ll want to attend the North Coast Music Festival, held from September 3rd to 5th on Northerly Island. Another popular music festival in the city is the Grant Park Music Festival, which features classical music at Millennium Park’s Jay Pritzker Pavilion. Find the 2021 line up here.

Fly on a helicopter

One breathtaking and heart-stopping way to see the city is to hop on a helicopter. You’ll be able to see astonishing views while on one of Chicago’s helicopter tours. Helicopter tours often fly over iconic sights such as Wrigley Field, Soldier Field, Magnificent Mile, Lake Shore Drive, Willis Tower, John Hancock Building, Museum Campus, and more. These types of tours provide an exciting way to view the city from a unique perspective as well as a great time to take stunning photos and videos of Chicago. 

Play beach volleyball

North Avenue Beach, located in Lincoln Park, is a popular Chicago beach and features sand volleyball courts for anyone looking to bump, set, and spike. This is the perfect spot for athletes looking to break a sweat, or for others who just want to casually play a game of volleyball. Once you finish your game, you can take a dip in Lake Michigan to cool off and enjoy relaxing on the sandy beach.

See the city from the Skydeck

Of course, we couldn’t leave this traditional, yet impressive, Chicago gem off of our list. The Willis Tower is the tallest building in the Western Hemisphere. The Skydeck, located on the 103rd floor of the Willis Tower, offers both stunning and heart-pounding views. You can choose to stand out on the Ledge’s glass box, 1,353 feet in the air—if you dare. This is a great opportunity for a photo op, especially because of the jaw-dropping views located right beneath your feet.

Ride a jet ski on Lake Michigan

Experience the thrill of jet skiing, feel the wind in your face, and see the sights on Lake Michigan. You can rent a jet ski for a recreational adventure and ride along the Lakefront. Bring your family, a small group of your friends, or a significant other to jet ski alongside you. 

Experience 360 Chicago

360 Chicago will—literally—give you 360-degree views of Chicago far above the ground at 875 North Michigan Avenue, formerly known as the John Hancock Center. 360 Chicago now offers a thrilling new experience, called TILT. During your TILT experience, you will be extended out and over The Magnificent Mile and Chicago’s famous skyline, seeing unique, downward facing views from 1,030 feet. 

Cruise on the Lakefront Trail

Rent a Divvy bike from Chicago’s bike share program, and cruise along the Lakefront Trail. You’ll be able to see stunning views of Chicago’s skyline. Discover some of the best views on the trail near Museum Campus, outside of Adler Planetarium. The trail juts out into this lake at this point, making it a perfect spot to see the city’s entire skyline. Further along the trail, you’ll be able to ride to Navy Pier, past Ohio Street Beach, and onto Lincoln Park. 

Try new foods

Give your taste buds an adventure by trying new foods around the city. Of course, if you haven’t already tried traditional favorites like deep dish pizza or Chicago dogs, you should definitely give them a taste. You can also travel to different neighborhoods located around the city, such as Wicker Park, West Loop, Chinatown, Lincoln Park, River North, or Streeterville to try new types of food. Streeterville, located next to The Magnificent Mile, has an array of restaurants to choose from, including the Albert, a contemporary restaurant. Experience unique menu items at the Albert like their starter, tomato braised and charred octopus and entrees such as spring lamb white bolognese and rigatoni. 

Planning your trip

Whether you choose to visit Chicago this summer or another time in the future, you’ll have an enchanting experience. After you’ve selected your travel dates, you’ll need to decide where you’ll stay on your trip. Consider booking a hotel located in the heart of the city, like Hotel EMC2 in Streeterville. It’s conveniently located close to many of these exciting activities and is also next to many other iconic destinations. Next up, pack your bags with essentials like comfortable walking shoes and sunglasses. Now you’re ready for your upcoming trip to Chicago filled with breathtaking adventures and spectacular sights. 

Need a place to stay when visiting Chicago? Book your reservation here.