Travel Hackers: #DiningDash Friday Is Tomorrow! Join The Fun And Win 2,500 Miles!

Of all the ways to travel hack, one of my favorites is to eat my way to free trips.

If you follow the world of travel hacking at all, you already know about credit cards, bonus miles and manufactured spending. But did you know many major U.S. airlines also offer a dining program?

Tomorrow, Friday, February 6, I’ll be joining my friends Chris Guillebeau and Stephanie Zito, travel hackers extraordinaire, as I eat my across Portland in attempt to reach VIP status with the American Airlines dining program in just one day for less than $50. If I make it, I’ll earn 5 miles per dollar (!) every time I eat out for the rest of year.

We call this fun and gut-busting foray the #DiningDash challenge. You’re invited to join us from wherever you are and, if you do, we might send you 2,500 miles.

Read on for details.

(Attn. Portlanders: Join us for our final stop of the night at the Triple Nickel—a ridiculous dive bar—on SE Belmont at 9:00PM)

Image courtesy of The National Review
Image courtesy of The National Review

Will Eat For Miles: How To Earn Frequent Flyer Miles From Restaurants

Here’s how this whole silly dining miles bonanza works.

A number of US-based airlines partner with a company called Rewards Network who maintains a big list of restaurants, coffee shops, diners, and bars. Each time you eat at one of these restaurants, you earn a “qualified dine” and frequent flyer miles equal to the amount of your bill.

Here are the most popular programs to join (you can only join one at a time):

  • American (2,000 mile sign-up bonus)
  • United (2,000 mile sign-up bonus)
  • Delta (2,500 mile sign-up bonus)
  • Alaska (500 mile sign-up bonus)

Once you sign up, you register all your credit/debit cards with the program and automatically earn miles each time you eat out.

At first, you’ll earn one mile per dollar. But once you earn VIP status by completing 12 dines, you’ll earn five miles per dollar for the rest of the year! Remember, this is in addition to any miles you earn simply for spending money on your credit or debit card. So nice!

Most people don’t even complete 12 qualified dines. Some do, but get to it so late the benefits of 5x miles expire soon after. The strategic travel hacker, though, (that’s you!) gets them out of the way quickly, cheaply and early in the year. Then, you stockpile miles like a squirrel stockpiles nuts for winter.

That’s what we’ll be doing tomorrow, and here’s how you can join us.

#DiningDash Friday: Join Us On Instagram, Win 2,500 Miles!

If you want to be a part of the gut busting fun, you can participate from wherever you are. Here’s how:

  1. Sign up for one of the dining programs above and register your credit and debit cards.
  2. Use the search tool (available inside your account) to find participating restaurants near you.
  3. Take a selfie for each dine and tag it with #DiningDash on Instagram. Follow the hashtag to see what everyone else is up to.

You can participate to whatever extent you want, but we’ll send 2,500 United Miles to the first person who finishes 12 qualified dines. If you think that’s you, just send an email to with a link to each Instagram photo.

If you want to chat #DiningDash strategy, join this thread over in The Lab.

Portland: Celebrate With Us

Whether you take part in the challenge or not, if you’re in Portland come out for a celebratory drink with us at 9:00 PM at The Triple Nickel—a hipsteresque dive bar—on SE Belmont. The drinks won’t be great, but the 5x miles will be!