Best High-risk activities in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

Filter High-risk activities in Chicago

Chicago & North Shore Stand Up Paddle board lessons & tour

Learn how to safely paddle board on the beautiful Lake Michigan. You will gain paddling knowledge, ability, and confidence, resulting in both a great time and lasting skills for all future paddling adventures!

$150.00

From

Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

8 Reviews

Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise

Take an exciting educational adventure aboard Tall Ship Windy with this cruise from Navy Pier in Chicago. Watch as Great Lakes history and maritime traditions come to life.

$29.00

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Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

2 Reviews

Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

$99.99

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Chicago: Full-Day or Half-Day Bike Rental

9 Reviews

Chicago: Full-Day or Half-Day Bike Rental

Choose between a full-day or half-day bike rental and explore Chicago at your own pace.

$23.99

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Chicago: Private Helicopter Tour of Chicago Skyline

11 Reviews

Chicago: Private Helicopter Tour of Chicago Skyline

Join this daytime helicopter tour over Chicago and enjoy views of the city's famed architecture. Choose between 10 and 20-minute flight options and gaze at sights like Willis Tower and Wrigley Field.

$187.50

From

iFLY Chicago Lincoln Park: First Time Flyer Experience

6 Reviews

iFLY Chicago Lincoln Park: First Time Flyer Experience

Defy gravity in a state-of-the-art wind tunnel and feel the thrill of a simulated skydive. Freefall in safety and experience the thrill of an indoor bodyflight.

$73.57

~~From $98.09~~

Chicago Lakefront: Seadog Speedboat Ride

322 Reviews

Chicago Lakefront: Seadog Speedboat Ride

Enjoy Chicago's iconic skyline with a speedboat tour of Lake Michigan. Depart from Navy Pier and feel an adrenaline rush as you take in views of the city from a different perspective.

$41.59

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Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

76 Reviews

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

Watch the fireworks dance over Chicago's skyline on this popular 60-minute speedboat tour. Enjoy panoramic views of a magnificent fireworks display from the waters of Lake Michigan. Perfect for a romantic evening or a memorable night out with friends.

$59.44

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Chicago: 360 Chicago Observation Deck Fast Pass Ticket

2 Reviews

Chicago: 360 Chicago Observation Deck Fast Pass Ticket

Enjoy fast-track access to the 360 CHICAGO Observation Deck, sitting 1,000 feet over Chicago’s legendary Michigan Avenue. Take in panoramic views of this vibrant city from a privileged location.

$55.00

From

iFLY Chicago-Rosemont First Time Flyer Experience

4 Reviews

iFLY Chicago-Rosemont First Time Flyer Experience

Defy gravity in a state-of-the-art wind tunnel in Chicago-Rosemont and feel the thrill of a simulated skydive. Freefall in safety and experience the thrill of an indoor bodyflight.

$69.52

~~From $92.69~~

Chicago: 45-Minute Private Helicopter Flight for 1-3 People

62 Reviews

Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Enjoy a view of the Chicago skyline from a helicopter, with the extra thrill of a “doors off” flight experience during the summer. Learn interesting facts about the city’s history.

$849.00

From

Chicago: Private Catamaran Sailing for up to 12 people

This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest chartered Catamaran.

$1,500.00

From

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