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Duration: 35 minutes


Ready for a high-flying adventure over Chicago? Hop aboard a private, single-engine airplane and get ready to experience the city like never before! Your expert pilot will whisk you away on an epic tour that showcases all the must-see spots, from iconic landmarks to stunning lakefront views.

✈️ Soar above Chicago's landmarks and lakefront in a private, single-engine airplane

🏟️ Feast your eyes on iconic spots like Wrigley Field, Navy Pier, and Millennium Park

🔄 Experience the magic all over again as you return to Chicago Executive Airport

🌟 Enjoy the expertise of an experienced pilot with a stellar reputation and decades of flight time


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.


Practical information

Any restrictions to participate?

  • Age: All ages are welcome. 
  • Weight: Individual passenger weight cannot exceed 275 pounds and the combined weight of the group cannot exceed 600 pounds.
  • Height: Participants taller than 6’6” may be uncomfortable in the plane. 
  • Physical limitations: Participants must be able to enter and exit the aircraft on their own or with assistance from a member in their group. The pilot is not able to assist passengers in boarding the aircraft.


Who can you accommodate for?

  • Children: Children of all ages are welcome on the tour, however each child must have a dedicated seat and will need to use the same carseat they would use in a car. Participants must supply the carseats, as the pilot does not have them available.  
  • Individuals with disabilities: The facility where the experience takes place is wheelchair accessible. Individuals can participate, so long as they can get in and out of the airplane with or without assistance from a group member. The pilot is not able to assist passengers in boarding the aircraft. 
  • Pets: Well behaved dogs are allowed on the tour. The pilot loves dogs and partners with Pilots & Paws in his spare time.

What to expect on the day of the experience?

  • Duration: 35 minutes of flight time
  • What’s included: 35-minute guided plane tour of the Chicago lakefront. Friendly pilot with over 35 years of experience. 
  • Who will be present: The pilot and the participants in your group. There is a minimum of 2 passengers and a maximum of 3 passengers.
  • Spectators: Spectators are not allowed in the plane, but may be present at the airport at the time of take-off and landing. 
  • Photo/ video: You are encouraged to bring a camera or a phone to capture beautiful pictures of your whole experience.
  • Specific rules to follow: Smoking is not allowed on the aircraft.


How to prepare?

  • Weather dependency: This is a weather dependent experience. Safety is the pilots number one priority. Considering the weather is dynamic and conditions can rapidly change, the pilot is constantly monitoring the weather. When weather conditions are deemed unsafe for flying, you will be notified of cancellations as soon as possible. When flights are canceled due to weather, your pilot will work with you to find a time to reschedule your flight experience.
  • Arrival: Please arrive at the airport 15 minutes before your scheduled tour to allow time to meet your pilot, check in, and complete a safety briefing.
    • Please be advised, passenger arrivals that are more than 20 minutes after their scheduled flight time, will be charged a $20 late fee. Though unexpected events do happen, in order to keep our tour schedule and to respect the time of our other customers, it is important that we ask you to arrive on time.
  • Parking: Free parking is available at the airport and is within 50-100 feet of the building where you check in for your flight.
  • What to wear: The temperature inside the airplane is similar to the temperature outside the airplane, dress for comfort and consider bringing a sweater/sweatshirt.
  • What to bring: Feel welcome to bring bottled water or other clear beverages. It is recommended to bring a camera or a phone to capture beautiful pictures of your whole experience.
  • Restrooms: Restrooms are available at the airport facility.


Full description

Picture yourself in the cockpit of a single-engine airplane, with the wind in your hair and the city laid out like a sprawling playground beneath you. This isn't your ordinary tour – it's a whirlwind journey that'll have you buzzing with excitement from the moment you take off.

As you ascend from Chicago Executive Airport, the sprawling beauty of Lake Michigan's shoreline unfolds before you. Brace yourself for a visual feast as you cruise above the city, spotting iconic sights that make Chicago truly one-of-a-kind. From the majestic Baha’i Temple to the historic Wrigley Field, and the gleaming Navy Pier to the reflective allure of The Bean, you'll be checking off the city's greatest hits from your bird's-eye vantage point.

But that's not all – as you head back to the airport, get ready for a whole new perspective on the sights you just experienced. It's like hitting rewind on a blockbuster movie, only this time, you're in the director's seat! Plus, the pilot and owner's impressive 35 years of experience and over 10,000 flight hours mean you're in the safest, most capable hands.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 72 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 72 hours in advance means losing the value of your experience. $25 rescheduling fee, subject to waive for cause.

Duration: 35 minutes
Regular price $399
$399 Regular price $415 Sale price
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Here's what others have to say!



Based on 0 reviews

Alex S.

We threw a retirement bash and decided to do something epic. Our pilot made sure we felt totally at ease before takeoff and even doubled up as an incredible tour guide. The flight from start to finish was smoother than a jazz solo. Kudos for making our retirement celebration soar to new heights!

Taylor R.

I checked off a major bucket-list item, and it was beyond cool. Imagine piloting dreams or a love for Chicago's skyline meeting reality – that's this tour. Our pilot was an encyclopedia of knowledge, making safety a second skin. Luck was on our side, as the weather played ball for a stunning sunrise flight. The smooth ride was like gliding through dreams. The vistas were a masterpiece. Count me in for an encore, and next time, I'm bringing the kids!

Jordan M.

I had a surprise plan for my husband's flight, and let me tell you, safety was paramount. Our flight schedule was changed up a few times due to safety checks – the pilot's commitment to 100% safety was reassuring. With a thorough rundown on the sights and sensations, the flight felt like a breeze (thanks, good weather). We've got awesome photos and a memory etched in our hearts, with the pilot's dad jokes adding extra charm. You can tell this pilot's a sky veteran. If safety's your jam, book this flight!