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The Strangest Way I’ve Ever Earned Airline Miles

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If you’re more than a novice in earning points or miles, then you know there are many ways to increase your balance. There are the obvious ones like flying, staying in hotels, or using a co-branded credit card. Then there are the lesser-known options, like booking hotels through airline travel portals (Delta Stays, AAdvantage Hotels), or using shopping portals like United MileagePlus Shopping to earn miles for purchases you would make anyway.

But one of the most overlooked methods are the dining portals. Nearly every major U.S. airline has one, and they’re all run by the same back end company. We’ve reviewed how to sign up for these programs in this post.

That leads me to one of the strangest ways I’ve ever earned miles.

The Day a Cookie Earned Me Airline Miles

On a recent trip to New York City, we packed our schedule with Broadway shows—five shows in three days, to be exact. That didn’t leave much time for sit-down meals. On one of the days, with only an hour between shows, neither my wife nor I were very hungry. We decided to swing by one of our go-to spots near Times Square, Junior’s.

We know that the Manhattan Junior’s near Times Square isn’t quite the same as the original Brooklyn location. If you want to experience that one, it’s worth the trip.

In this case, we just stopped at the walk-up counter and grabbed a black and white cookie. If you’re unfamiliar, they’re a New York classic: part cake, part cookie, with one half covered in chocolate fondant and the other in vanilla icing. (Here’s an explanation of the Black and White cookie tradition.) It was the perfect snack to tide us over before the show.

The Happy Surprise

Two days later, I got an unexpected email from SkyMiles Dining:


Our cookie purchase had earned me 15 Delta SkyMiles. Sure, that’s only worth about 15 cents, but it’s 15 miles I wouldn’t have otherwise earned. It also made me think: could this be a low-cost hack for reaching VIP status in SkyMiles Dining?

The Cookie Hack

Here’s how the program works:

Just dine 11 times before the end of the year at participating SkyMiles® Dining restaurants to become a VIP member.

As a VIP member, you get:

So if you live in an area with participating restaurants, strategically buying low-cost snacks (like a cookie) could get you to VIP status faster. For a $100 dinner, VIP status earns you an extra 200 miles compared to the standard rate.

Final Thought

Over the years, I’ve earned points and miles in some unusual ways, but this was the first time it happened from buying a single cookie.

Have I earned a fortune? Not exactly. But every mile counts, and being enrolled in dining programs means you can pick up unexpected bonuses like this.

What’s the strangest thing you’ve ever earned miles or points for? Let me know in the comments!

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This post first appeared on Your Mileage May Vary

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