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Urban Adventures in Chicago

Urban Adventures in Chicago

Ready to do even more than sipping, shopping and strolling your way through the Windy City? We challenge you to take on some of Chi-town’s little known—ridiculously heart-pounding—outdoor adventures.

The Windy City is renowned for many things—deep-dish pizza, the Miracle Mile and some of the country’s best sports teams—but it’s not the first place that comes to mind when you think of outdoor adventures. That doesn’t mean, however, that you can’t get yourself into some heart-pounding, high-adrenaline hijinks in the Chicago area. In fact, whether you’re seeking thrills by land, by sea—or by air—you can find some serious action in and around this urban jungle. You just have to know where to look!

Go Sky Diving 

There are few things more daring than jumping out of a perfectly good airplane—so impress your friends and get the deed done through Skydive Midwest. You’ll travel 14,500 feet into the sky in just eight minutes as you fly on a King Air twin-engine turboprop. From there, you’ll lose your mind (temporarily) as you fling yourself from the side door of the plane and watch as the earth rushes up to meet you. All too quickly, the time will come for you to pull the ripcord, slowing your descent and allowing you to take in 360 degree aerial views of the Chicago skyline, Lake Michigan and downtown Milwaukee from above.

Learn Trapeze

Ever wonder what it would be like to run away and join the circus? Indulge the urge to leap, flip and swing like a true performer at one of the Chicago-based outposts of Trapeze School New York, located on Broadway Armory Park (indoors) and Belmont Harbor in Lincoln Park (outdoors). You can enroll in a variety of classes including “Flying Trapeze,” “Beginner Silks,” “Tightwire” and “Acrobatic Yoga and Conditioning,” all of which will bring you a little closer to the sky…and your childhood dreams of performing under the big top.

Zipline Through The Forest

Just outside of the downtown Chicago area, you’ll find local woodlands that are waiting to be explored. One of our favorite ways to do just that: Sign up for a treetop adventure through Zip Chicago Canopy Tours. The experience, which is design to send you like a jungle creature from tree to tree, includes eight ziplines spanning from 150 to 1,000 feet, as well as two suspension bridges located 90 feet off the ground.

Jet Ski or Paddle Board at Montrose Beach 

Montrose Beach, located in Uptown Chicago, is a scenic beach known for its wide array of water sports. Here, you can try stand-up paddleboarding (a mix of surfing and kayaking) or rent a jet ski and zoom through the waters at high speeds, bouncing on waves as the water splashes your skin. Kayaking is also an option, allowing you to navigate Chicago’s waters as the captain of your own vessel. 

Take off on a Speedboat Ride 

Looking to fulfill your need for speed? Speedboat Rides “Seadog Extreme” propels guests 45 miles per hour over open water for a wet and wild ride that features sharp twists, full throttle slalom runs and hairpin turns.

Experience The Thrill Of Rock Climbing 

While you won’t find any high peaks in Chicago, you can head to Fitness Formula Clubs in Old Town to experience both beginner and expert routes on the gym’s rock climbing wall. If you’ve never climbed, you maybe shocked to learn that the skill is both easy to pick up—and incredibly challenging to master. We recommend grabbing a buddy for your very first experience on the wall; you can cheer each other on, recommend which direction to travel and reward yourselves with a much deserved meal afterward.

Hike In Humboldt Park 

Boasting 219-acres of sports fields, gymnasiums, wetlands, fishing areas, a beach, lagoons, ponds, bird watching, gardens and scenic trails, Humboldt Park is a true destination for adventure and nature lovers within Chicago. The Humboldt Park Lagoon is the center of the action, where you can fish, view more than 145 bird species and explore the extensive network of trekking trails.

While Eagle Creek is here to provide tips and insights on travel, we cannot accept any responsibility for any potential consequences arising from the use of this information. Always conduct your own research and use your best judgment.  

Jessica Festa, a New York native, is a world traveler who is always looking for a new adventure. She stays active through hiking, cycling, and dance, and loves nothing more than her backpack. Follow her travels around the world at Jessie on a Journey and at Epicure & Culture

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