Chicago Extreme Sports

Explore top extreme sports tours in Chicago including skydiving, paddleboarding, boat adventures, and day trips for adrenaline seekers. Book your thrill today!

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Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests e

From $1,800.00 USD

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which prov

★ 5.0 (40)

From $90.00 USD

Chicago to Mackinac Island Scenic Tour

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel thro

From $685.00 USD

Chicago-Milwaukee Small Group Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller

From $485.00 USD

Chicago-Rosemont Indoor Skydiving with Two Flights

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 s

★ 4.4 (34)

From $126.00 USD

Flyover in Chicago

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover

★ 4.7 (726)

From $27.95 USD

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water

★ 5.0 (2)

From $105.00 USD

Mackinac Island Private Day Tour from Chicago

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embrace

From $1,350.00 USD

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, wher

★ 3.0 (2)

From $450.00 USD