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Chicago Learn to Fly Experiences

At Cloud 9 Living we offer over 1,900 top-rated experiences, easy returns and exchanges, and thousands of positive reviews from our happy customers. Book or gift an experience today!
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  • Reach new heights with Chicago Learn To Fly experiences that are simply air-mazing!

    The Windy City is one of the most picturesque places to learn how to fly. With its grand skyscrapers, magnificent Lake Michigan waters and impressive shoreline, there's no better place to try pilot lessons.

    Take to the skies to learn to fly a Cessna! From airport arrival and pre-flight instruction, to landing and everything in-between, an FAA certified flight instructor is your personal guide to the world of piloting an airplane.

    Soak up some solid ground instruction and learn the basics about aviation, then assist the pilot with the pre-flight aircraft inspection. Before you know it, it's time for your pilot to complete the taxi and take-off. Your hands-on lesson begins as soon as a safe cruising altitude is reached. The controls are all yours as the instructor coaches you through the fundamentals of flying lessons. Once the pilot lands you safely on the ground, enjoy a debriefing and ask questions pertaining to any further interest you may have for further pilot lessons or licensing.

    Deviate ever so slightly from the flight lesson norm with a unique Lake Geneva Aerial Getaway! Delight in learning to fly a Cessna in all the same ways featured in the airplane lesson option — but with the twist of a 2-hour round trip! Break up the flight with a stop at the Grand Geneva Spa and Resort for a delicious lunch; admire the breathtaking landscapes there and back, including the Chain of Lakes, Lincolnshire, Mundelein, and more.

    Believe it or not, the Learn To Fly experiences in Chicago feature more than just airplanes! Learn how to fly a helicopter, complete with instruction in flight theory, operations, and hands-on maneuvers in an OH-6A aircraft. And the more the merrier — bring a passenger along for the ride!

    And for an extra-distinct way to soar, give an Ultralight Lesson and Flight a go! This unique form of aviation is comes as an airplane and glider-like hybrid. Feel the thrill of open air as you cruise through the skies in the powered (but serene) aircraft. This remarkable pilot lesson will cover the basics of flying this intriguing aircraft, in addition to take-off and landing. And without a doubt, it will leave you with tales to tell for years to come.