Top 8 Adventure Tours in Chicago

Destination: Chicago.
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 provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
Known For: Chicago Adventure Tours, Chicago Speed Boat Rentals, Chicago Small Group, Chicago Zombie, Chicago Excellent Quality, Chicago Historical Tours, Chicago Jet Boat Rentals, Chicago Zombie Slice, Chicago Extreme Sports, Chicago Water Tours.
Duration: Around 1 hour and a half.

Destination: Chicago.
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 Lake Michigan, while enjoying the views, and the fresh air! Fun for all ages! You can join our friendly crew, to help raise one of the many sails on Windy, or just relax, and let others do the work! Windy has a full bar, and a gift shop, to help you enjoy the sail.
Known For: Chicago Likely to Sell Out, Chicago Sustainable Tours, Chicago Water Tours, Chicago Sailing, Chicago New Product, Chicago Adventure Tours, Chicago Likely To Sell Out.
Duration: Around 1 hour and a half.

Destination: Chicago.
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 like; pausing to explore further on your own. Take in the sights of the public art—including the famous "Cloud Gate," otherwise known to locals as "The Bean"—and hear the stories behind their creation. The GPS-enabled guide will stop and start the professional commentary automatically as you explore the area. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months. This isn't an entrance ticket. Check opening hours before your visit.
Known For: Chicago Historical Tours, Chicago Adventure Tours, Chicago Audio Guides, Chicago Walking Tours, Chicago Nature Walks, Chicago Private Sightseeing Tours.

Destination: Chicago.
A helicopter tour of downtown Chicago is a unique and thrilling way to experience the Windy City. From high up in the sky, you'll be able to take in breathtaking panoramic views of Chicago's iconic skyline, world-famous landmarks, and bustling city streets.
Known For: Chicago Helicopter Tours, Chicago City Tours, Chicago Adventure Tours, Chicago Small Group.
Duration: Around 10 minutes.

Destination: Chicago.
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 Chicago from the water. Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline!
Known For: Chicago Water Tours, Chicago Adventure Tours, Chicago Speed Boat Rentals, Chicago Jet Boat Rentals.
Duration: Around 30 minutes.

Destination: Chicago.
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 landmarks such as the Gold Pyramid House and the stunning Bahāʾī temple. The 85-mile bike ride will bring you right to your boutique inn where your bags will be waiting for you. The following day your guide will take you to the beach where you can kayak or just enjoy some much-deserved lounging. After this you will visit the Apple Barn for a delightful day of seasonal apple or strawberry picking, followed by a stop at their bakery. Don't forget to bring your ID for the wine tasting; they often feature live music and are very family-friendly! Will give you time to explore the shops and ice cream parlors in the charming downtown area before packing the car to drive you back to Chicago.
Known For: Chicago Mountain Bike Tours, Chicago Bike Tours, Chicago Adventure Tours, Chicago New Product, Chicago Multi-day Tours, Chicago Overnight Tours, Chicago Small Group.
Duration: Around 2 days.

Destination: Chicago.
Book early, as these tend to sellout! you are free to move about the ship, while the music plays, everywhere.
Known For: Chicago Sailing, Chicago Water Tours, Chicago Likely to Sell Out, Chicago Music Tours, Chicago Likely To Sell Out, Chicago New Product, Chicago Adventure Tours, Chicago Art Tours.
Duration: Around 2 hours.

Destination: Chicago.
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 provide effortless rides through the city, eliminating worries about traffic and parking. Experience the joy of biking while saving on gas and insurance costs. - Convenient location on Clark Street in Lincoln Park - Free demo test ride available - Ideal for leisurely exploration or thrilling rides - Expert advice to help you choose the right e-bike model
Known For: Chicago Adventure Tours, Chicago E-Bike Tours, Chicago Nature and Wildlife Tours, Chicago Bike Tours, Chicago Mountain Bike Tours.
Duration: Around 2 hours and a half.