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Chicago Flying Experiences

Want to earn the title of "world's best gift giver"? Start here. These Chicago flying experiences take ordinary celebrations to a whole new altitude. We're talking about scenic airplane rides over Lake Michigan, hands-on flight lessons, and even exhilarating skydiving trips just outside the city. No matter the flight, these experiences are the perfect picks for birthdays, Father's Day, Christmas, anniversaries, or those casual "I was just thinking of you" moments.

A bird's eye view of the Windy City

Chicago is impressive from the ground. But from the sky? It's absolutely spectacular. Just imagine your loved one soaring across the sky, admiring Lake Michigan, Millennium Park, Willis Tower, Navy Pier, and more. Now that's what we call a gift they'll never ever forget.

Which Chicago flying experience should I gift?

That depends on who you're shopping for. For the aspiring pilot, a hands-on flight lesson lets them take the controls alongside a certified instructor. For the adventurer, skydiving delivers an unforgettable adrenaline rush. And for the person who loves sightseeing with a twist, scenic helicopter tours offer a front-row seat to Chicago's skyline, shoreline, and beyond. Whatever their personality, there's a flight here with their name on it.

How to gift an experience through Virgin Gifts

We make every step easy peasy. Just pick their experience, send an instant e-voucher, and let them schedule their flight on their terms. With flexible booking, easy exchanges, and no expiration dates, gifting experiences with Virgin Gifts is a piece of cake.

All Flying Experiences in Chicago, IL

16 Products

How it works...

4 easy steps to memories that will last forever

  • 1
    Take your pick

    Take your pick

    Select

    Select from our range of over 5000 experiences.

  • 2
    No time limit

    No time limit

    Timeless

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

  • 3
    They pick a date

    They pick a date

    Choice

    Our vouchers are date-free, so they can pick a time that suits them!

  • 4
    Unforgettable

    Unforgettable

    Memories

    We believe in delivering amazing experiences, your gifting experience should be no different.

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Frequently Asked Questions

Get ready to take off! In Chicago, you can enjoy scenic flights over the stunning skyline, learn to fly with hands-on lessons, take thrilling helicopter tours, or even try your hand at a flight simulator.

Chicago has its charm in every season! Spring and summer offer clear skies and vibrant views, while fall brings stunning autumn colors. Just remember, winter can get a bit chilly, so bundle up if you’re flying during the colder months!

If the weather isn’t cooperating, no worries! Your safety is our priority. In such cases, your experience will be rescheduled, so you can enjoy your flying adventure when conditions are just right.

Yes, you can! Chicago offers fantastic flying lessons where you can get hands-on training in a real aircraft. With experienced instructors by your side, you’ll be soaring through the skies in no time!

Absolutely! Imagine gliding over the iconic Chicago skyline, flying above Lake Michigan, or spotting famous landmarks from the air. Chicago’s flying experiences are truly one-of-a-kind. 

Absolutely! Gift certificates are a fantastic way to treat someone special to a flying adventure in Chicago.

If flying makes you a bit anxious, we recommend starting with a scenic flight or helicopter tour. These experiences tend to be smoother and can help ease you into the joy of flight. Plus, the stunning views will distract you!