Man Checks In For Southwest Airlines Flight From Chicago To Orlando. Then He Finds Out He’s The Sole Passenger On Board

by Madeleine Wagner | July 18, 2026 | 0 Comments
note with a message on it (l) man shares traveling experience (c) Southwest airlines (r)
@jeromestone3/Tiktok, Photo by Sven Piper on Unsplash

It’s the air travel dream. Flying alone on a private plane to the happiest place on Earth.

For one man traveling to from Chicago to Orlando, that dream unexpectedly came true—on a commercial flight.

Fitness buff Jerome Stone (jeromestone3) was in the boarding area for his Southwest Airlines flight out of Chicago when he started filming. “I’m flying home today, by myself,” he says.

But he didn’t mean he was flying without a companion: he was the only passenger on the flight. It was no puddle jumper that only seats a dozen or so, either, but a normal-sized jet with six seats in each row. Truly an original experience.

“Fly Private With Me”

“Come along and fly private with me,” he says with a little laugh.

After he found out he was the only passenger on the flight, he started filming his interactions with the Southwest Airlines crew. All agreed he’s the VIP. “You’re the most important passenger on this flight, and the only one,” a member of the flight crew told him.

Curious about the situation, Stone asked the flight attendants and the pilot if they’d ever seen anything like this before. The answer was a resounding “no.” Stone settled in to make the most of his once-in-a-lifetime opportunity.

Like it was any other flight, the crew reviewed the safety protocols. An amused Stone filmed the review of how to work the under-seat inflatable life preserver.

Then they were off, and the crew continued to make the flight special for him. They showered him with snacks, a tequila cranberry drink, and some small souvenirs to commemorate the experience.

At one point a crew member even fit a paper crown to his head.

Stone says, “This gave me a taste of my ultimate goal, which is flying private.” He adds that he doesn’t have “$20,000 to drop on a flight, so this will have to do.”

In an email to BoardingArea, Stone confirmed that the crew let him sit wherever he wanted, even after upgrading his seat. Then, during the flight they took pains to make it a one-in-a-million experience. He said “the crew making it memorable” was his favorite part.

“Shout out to the crew and shout out to Southwest, I’ll definitely be flying again,” he says.

When asked if there’s anything they officially or even unofficially do when a passenger happens to hit this travel jackpot, Southwest told BoardingArea via email, “We give our employees broad leeway to deliver hospitality, using their own creative spirit, to all customers at all times.”

Why Would A Plane Fly With One Passenger?

In the comments section, the envy and curiosity are palpable. But so too are the good vibes. The first comment is from the verified Southwest Airlines account.

“OUR VIP. Thanks for sharing the skies with us!!” Southwest wrote from its verified account.

While dennifromtheblock asked, “Somebody tell me how this happens.”

Numerous people offered explanations.

“This is something that happens often. They need those planes in certain cities, Hubs, etc…” explained juliek70.

A person who said they’re a flight attendant added, “Delta FA here, once had 8 people…moved all to first class and loved treating them like royalty. The plane was needed in another city.”

How Often Do Commercial Flights Carry Only One Passenger?

Imagine, being comfortable in your seat, with plenty of room to stow your luggage, and miracle of miracles: no one listening to their phone without earbuds. It’s enough to make a traveler want to crack the code on how to be the only passenger on a commercial flight. But there’s really no trick to it. Just luck and logistics.

Often, when flights are empty of passengers, the flight still serves a purpose. It’s highly likely that the aircraft is carrying freight. The site How Stuff Works reports that the U.S. Postal Service alone “leases space on 15,000 of the approximately 25,000 scheduled passenger flights each day. Often, airlines make about 5 to 10% of their revenue from hauling freight.”

However, the users in the comments are correct too. The Points Guy says that the reason flights with only one person don’t get canceled likely comes down to logistics. “Airline timetables rely on planes being in specific locations at specified times. Most planes don’t do out-and-back runs from hubs, instead flying to a number of destinations along a scheduled route.”

BoardingArea reached out to Southwest Airlines via their email. We will update this article when they reply to us.

@jeromestone3 I was the only passager on my flight @Southwest Airlines #fyp #travel #planes #flying ♬ original sound – Jerome Stone
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