Top Chicago Extreme Sports

Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training session from a flight instructor. Learn how to safely float in a 1,400-horsepower vertical wind tunnel that generates a wall-to-wall cushion of air, commonly used by professional skydivers. Experience the thrill of skydiving without having to hurl yourself from an airplane, and no experience is necessary. Once inside the enclosed space of the flight chamber, a tunnel operator slowly increases the wind speed until you and your instructor are airborne. Feel your adrenaline pumping as you 'free fall' at wind speeds reaching 180 mph (290 kph). The stable wind flow keeps you from falling off the column of air, and your instructor is on hand at all times to guide you. The first-time flyer experience takes about 75min. Each session includes up to 12 people, but fly one-on-one with your instructor in the wind tunnel twice for 60 seconds.

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.

Looking to try something new and fun? We’re excited to introduce you to the sport of axe throwing! This thrilling traditional Canadian backyard pastime is now bigger than ever in urban communities. With the help of our talented axe throwing coaches, guests are able to share our passion for nailing the bullseye. No experience necessary, all skill levels are welcome!

Studio W.I.P. by Native 312 Events offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Street Art as we learn about some different styles and techniques with guest artists. Then you get your hands dirty as you walk around our gallery setting and test out your skills in different mediums like aerosol spray and stencil. At the end of your workshop you will be able to go home with your own piece of art!

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City, the 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers, including Willis (Sears) Tower. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! Upgrade your ticket onsite to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or grab refreshments at our newly CloudBar.

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain. Enjoy the breeze as you glide effortlessly to the most popular Chicago tourist attractions along the Chicago lakefront: the Museum Campus, the Shedd Aquarium, the Field Museum, and of course Soldier Field, home of the Chicago Bears. You can't go wrong with this perfect sightseeing tour.

Chicago CityPASS® — Discover Chicago's best attractions at one great price with an easy to use mobile ticket. Spend less, experience more. Save 48% or more on prepaid admission to 5 must-see attractions: • Shedd Aquarium • Skydeck Chicago Plus your choice of admission to 3 of the following attractions: • Field Museum • Art Institute of Chicago • Museum of Science and Industry • 360 CHICAGO Observation Deck • Adler Planetarium • Shoreline Sightseeing Architecture River Tour

Delve deep into the world of natural history with this Field Museum All Access Pass in Chicago.  Your pass includes access to all ticketed exhibitions and one 3D movie.  Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents. Don't forget to meet Maximo, the museum's newest titanosaur at over two stories tall!

Explore over 40 million artifacts, including SUE, the world’s largest, most complete T. rex ever discovered! Discover 23 mummies in a recreated Egyptian tomb, our dazzling Gem Hall or journey to the powerful Aztec empire! Meet Maximo our newest titanosaur at over two stories tall! The health of our guests and staff is always our top priority and we welcome you back to safely explore nearly half a million square feet of open gallery space.

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!

See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night. View Buckingham Fountain's romantic evening light show with the illuminated skyline as a backdrop. This evening fireworks tour glides along the lakefront to our secret spot for watching Navy Pier's Fireworks display. It's difficult to decide which is more spectacular — the fireworks or the Chicago skyline in its evening splendor! A perfect family activity, this is one of our most fabulous Chicago Segway tours.

Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary walking tour, complete with a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef sandwich, brownies, as well as a VIP upgrade option that includes 3-samples of locally crafted beer (you can purchase this option upon arrival for $19.99/person). Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building, all the while regaling you with tales from Chicago’s rich food-centric history. This tour is sure to make memories that will last a lifetime!