Chicago Adventure Tours

Explore exciting adventure tours in Chicago including helicopter flights, speedboat rides, sailing, electric bike tours, and self-guided walks around Millennium Park.

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2 Day Private Tour Chicago to Mackinac Island Exploration

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages preva

From $2,700.00 USD

Chicago Helicopter Tour: Loop Tour

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighbor

★ 4.5 (12)

From $209.99 USD

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you lik

★ 4.6 (5)

From $14.99 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 Skyline Snap Tour Helicopter Flight Over Chicago

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the ci

★ 3.8 (19)

From $149.99 USD

Electric Bike Tours in Lincoln Park

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes provi

★ 5.0 (2)

From $85.00 USD

Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view

★ 4.1 (360)

From $39.27 USD

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lak

★ 4.7 (32)

From $91.23 USD

Small Group Bike Tours From Chicago to Lake Geneva

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see

From $449.00 USD