Chicago Flying Experiences
- See All 75 Experiences
- Action & Adventure
- City Tours
- Food & Wine
- Life & Culture
- Spa Packages
- Water Activities
Our Chicago Flying Experiences make for truly unique gifts they're sure to remember forever.
Cloud 9 Living's experience gifts are the perfect solution for anyone on your list and are guaranteed to bring a smile to your gift recipient's face.
Create a memory. Give the gift of experience!
A dream come true for those that have always wanted to learn to fly!
Learn to fly a helicopter as you take the controls of an extremely maneuverable OH-6A helicopter.
Experience the thrill of skydiving without the hassle of a plane and parachute when you go Indoor Skydiving!
If you have ever dreamed of flight or wondered what it would be like to pilot your own personal soaring craft, then you are a perfect candidate to venture into the world of hang gliding.
Experience the thrill of sky diving in Chicago at one of the most experienced skydiving centers in the country!
There is really nothing quite like the surreal thrill of flying an engine-less plane. Take the controls and find out for yourself what its like to soar over the midwest scenery during this Learn to Fly a Glider experience!
Get a birds eye view of the picturesque Illinois landscape on a Sunrise Hot Air Balloon Ride near Chicago!
Enjoy a romantic and tranquil flight over the Illinois countryside on a Private Hot Air Balloon Ride near Chicago!
Venture to Lake Geneva on this unique flying experience where you'll even have the opportunity to take over the controls!
Climb aboard for a magnificent sky high helicopter tour above Chicago!
Ultralight flying is an experience in freedom and excitement that is unmatched by any other activity.
Delight in the Windy City beneath your wings on Chicago flying experiences!
Be it a pilot lesson, aerial tour, freefall, or another type of air-venture — Cloud 9 Living offers outings perfect for folks who wish to fly!
Hope into the cockpit of a real Cessna 172 to learn how to fly an airplane! Enjoy expert training every step of the way from an FAA certified flight instructor. Assist with a ground inspection of the aircraft, while also receiving an overview of the fundamentals of aviation and flight operations. Then head to the runway and prepare for the ultimate hands-on flying lesson at cruising altitude! Soar over breathtaking Chicago scenery, piloting the plane all by yourself under the expert supervision of your instructor.
Can't get enough of the piloting lessons? Try your hand at hovering, ascending and descending as you learn to fly an OH-6A helicopter! Experience the exhilaration that comes with this unique form of flight, while enjoying unrivaled views of Chicago from right behind the aircraft's controls.
And speaking of scenic escapes, Cloud 9 Living's Chicago flying experiences offer unforgettable sightseeing opportunities! Helicopter tours are a perfect way to sit back, relax and enjoy magnificent bird's-eye views of the city's famous downtown skyscrapers or the serene backdrop of the Northwest suburbs. And for an even more peaceful float over the area, check out a Chicago hot air balloon ride. Leave the hustle and bustle of the city far behind, to savor the timeless ambiance of a sunrise or sunset flight — complete with a traditional champagne toast upon landing.
Craving an adrenaline rush in the air up there? Launch yourself out of a plane for some skydiving! Give hang gliding lessons a go. Or take a spin on one of the most unique and cutting-edge forms of flying ever to hit the aviation world, aboard an Ultralight lesson and ride. And if you're after even more pulse-pounding adventures, boldly accept the top dog (or Top Gun) of flying lessons: a Fighter Pilot for a Day challenge! This friendly competition in the skies comes with sleek combat jets, top-notch training from real military pilots, authentic dogfights, laser-ammo, and plenty of G-force — along with a lifetime of stories to boot.
The sky is truly the limit for making memories on Chicago flying experiences like these!