Outdoor activities near Chicago
9 bookable experiences
Hikes, water and open air within reach of Chicago — the trips worth leaving the city for, with the gear and the guide included.
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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 city’s iconic architecture, including Soldier Field and the…
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 Chicago from the water. Seadog offers fun for the whole…
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 Lake Michigan, while enjoying the views, and the fresh air!…
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, neighborhoods, and waterfront views. The flight begins near the…
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 provide effortless rides through the city, eliminating worries…
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 like; pausing to explore further on your own. Take in the…
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 landmarks such as the Gold Pyramid House and the stunning…
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 provides a unique and interesting touch to the normal tour…
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 prevails. This tour includes a beautiful drive through the…
Prices and availability last checked 2026-09-13. Both are confirmed on Viator before you pay.