7 Strange (and Legally Questionable) Ways People Have Scored Free Flights

  • In our series of “don’t try this at home,” let’s look at ways to fly for free.

Traveling sure is fun, but it’s also very expensive. Wouldn’t it be nice if you could fly wherever you wanted without paying a dime?

Well, the good news is you may be able to. Or at least you once were.


Over the years, airlines have had many kinds of offers, campaigns, and other promotions that allowed you to earn free flight miles. Most of them aren’t a thing anymore because people figured out a way to game the system, which looked bad on the airlines bottom line.

That, or the ways people abused the system ended up becoming illegal.

Here are seven examples of strange and dubious ways people have scored free flights. We can’t recommend you try any of them for yourself, though.

1. Collecting Coupons or Product Codes

Buy our product, mail us proof of purchase, and we’ll award you free air miles! If you grew up at any time before the 2000s, you might remember companies running these kinds of promotions.

They are rare today, though, since they weren’t exactly secure. People could (and did) find ways to make fraudulent receipts or product bar codes that they sent in without ever buying anything.

That, or they did exactly what the promotion was intended to do. Take, for instance, David Phillips, better known as the Pudding Guy.

In 1999, Healthy Choice Foods offered free air miles if you mailed in bar codes from their products. Phillips calculated that each air mile was many times more valuable than a single package of Healthy Choice pudding.

So, he spent thousands of dollars on pudding, emptying out entire stores. Yet, it was worth it, as he raked in 1,235,000 frequent flyer miles — in the process earning a lifelong Gold Member status with American Airlines.

2. Test Driving Vehicles

Here’s another promotion that you likely won’t find these days. Airlines would partner with vehicle manufacturers or car dealerships and award people frequent-flyer miles for test-driving cars.

Can you see the problem here? That’s right — you just needed to drive the car, not buy it.

So, people would go around driving cars they had zero intention of ever buying. Car dealerships lost out on sales and gas money, while the airlines had to hand out discounted or free flights.

In some cases, the dealership would just give you the miles without even touching the promotional vehicle. That’s because whatever contract they had with the airline earned them a profit, much to the airline’s detriment.

3. Flying Nowhere

Sometimes, if you want to fly somewhere for cheap, the best trick is to fly somewhere completely different. Some people engage in what are known as strategic mileage runs, flying to places just to earn frequent-flyer miles.

It comes down to simple math. Imagine you’re just a few miles short of scoring a free flight across the country.

That flight might cost you more than $1,000 if you paid in full. But if you buy a flight to the next town over for $200 and get the miles you need, you’ll save a lot of money — even if you have to figure out a way to get back home cheap.

Additionally, some airline loyalty programs require you to make a certain number of flights to retain your membership. In these situations, people sometimes make very long, unnecessary trips because it’s simply cheaper in the long run.

4. Overbooking on Purpose

Here’s a trick that has been very popular in the past. Some folks would book a seat on a flight they don’t necessarily even want to take — because they know the flight will be overbooked.

They can then play the hero, volunteer to drop off the flight, and get compensated for their “inconvenience.” In the past, the compensation could be free flier miles or even cash.

These days, however, airlines have caught on to this practice, and they’ll usually just move you to another flight to your original destination for free. That, or their customer service has deteriorated just that much.

This practice can be a bit risky, as well. You could, for instance, easily earn free nights at a hotel you don’t want to stay at instead of frequent flier miles as compensation.

5. Buying Government Bonds

Back in the day, you could invest in U.S. savings bonds and earn frequent flier miles as you did so. That’s because the Treasury used to let you buy them with a credit card.

If you had an airline credit card that earned frequent flier miles for purchases, you could quickly rack up free flights. Really, if you planned to purchase bonds anyway, there was basically no reason not to do it.

These days, the Treasury no longer sells bonds by credit card. We probably won’t need to tell you why — the system was vulnerable to shady practices far more serious than earning a few air miles.

6. Working for an Airline

Well, here’s one way to earn free or heavily discounted travel. You could simply get a job with an airline or travel agency.

Many of them offer special deals or even free miles to their employees as part of their compensation package. Depending on the job, you may even get to travel for work.

On the other hand, you’ll have to travel for work. We’re just saying, it’s probably not worth going into the travel industry just for cheaper flights if you don’t actually want to do the work.

7. Pretending to Work for an Airline

If you don’t want to work in the travel industry, you could always simply pretend that you do. Fraudsters and con men of all kinds have scored free flights by fooling airlines into thinking they work for them.

For example, take Tirone Alexander. The 35-year-old earned free flights between 2013 and 2024 by posing as a flight attendant.

That said, he didn’t get on the plane in a fake uniform and serve coffee. During flight check-in, he simply ticked the “I’m a flight attendant” box and provided false airline employer information.

Apparently, no one ever bothered to check if the data was bogus or not. Alexander made more than 120 cost-free flights until he was caught.

Once again, though, don’t do this. Alexander has been found guilty of four counts of wire fraud, each of which carries a maximum sentence of 20 years in prison.

No free flight is worth that.