Buy Now, Book Later
Free Returns & Exchanges
No Expiration Dates
Instant E-Vouchers

Chicago Flying Experiences & Plane Rides

Explore the Windy City from sky-high! Soar over skyscrapers, take flying lessons, or try a hot air balloon ride. Choose from a variety of Chicago flying experiences & give you or someone else a chance to check something off the bucket list today.

11 Results
  • Location:
  • Experience Type:
  • Price:

All Experiences on this page have been loaded.

How it Works

Instant gifts. Lasting memories.
Your step-by-step guide to giving the ultimate gift.


Choose from 2,000+ experiences nationwide

Pick the perfect experience gift or buy an egift card and let your recipient choose their own adventure.


E-Voucher Delivered Instantly

After checking out, you can easily print or email your Experience Voucher. While delivery is instant, the memories will last a lifetime.


Easy to redeem or exchange

Your recipient can book their experience at their convenience either online or by calling us. And if they'd prefer to do another one, they can easily exchange it.


Create unforgettable memories

Our trusted vendors and passionate team will ensure that your recipient will be treated to the experience of a lifetime—making memories that will last for years to come.

Hassle-free Gifting

Our experienced team takes the risk out of gift-giving with handpicked experiences that are guaranteed to delight. We only work with top-rated experience providers and offer flexible policies to make giving a great gift a no-brainer—no matter who you're shopping for.

Learn More

Created with Sketch. Easy Returns & Exchanges

We offer 30-day returns or your recipient can easily exchange their gift for anything else in our marketplace, anytime—free of charge.

Created with Sketch. No Expiration Date

Our vouchers never expire, so your recipient can redeem them at their convenience.

Created with Sketch. Price guarantee

No markups, no added fees. You'll pay the same price as buying directly from our experience providers, but with the flexibility of easy returns and exchanges.

  • 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!