Win the Frequent Flyer Game and Explore the World

For many, frequent flyer travel can feel like a maze - exciting, but impossible to take advantage of. This guide attempts to simplify the landscape, help you develop a plan of attack, and send you on your next adventure - for free!

By: Dan Pierson

Save List
6 Saves

Feel like you’re constantly accumulating frequent flyer miles, but you never see any tangible rewards? You’re not alone. $16 billion in points and miles go unredeemed each year in the U.S., as consumers fail to understand and use the free travel they've earned. Airlines and the credit card companies they partner with have an incentive to claw back your dollars - but there are simple and actionable strategies you can follow, to make sure that your miles don’t go to waste.

My name is Dan Pierson, and like you, I'm all about getting outside and seeing new places. When I was 20, I spent six months learning to “hack” the frequent flyer system. I read every blog and pored over forums to understand how this mysterious system worked. In the decade since I’ve traveled all over the world for free by collecting millions of frequent flyer miles through a variety of methods - cycling the north and south islands of New Zealand, living and exploring through South America, and studying abroad in Europe. 

Backpack the Brewster Hut Track | Photo: Vincent Frascello

Travel has always been my passion, but I spent most of my time paying the bills at tech startups in San Francisco. I always dreamed of bringing work and play together - and finally, earlier this year, I made it happen by starting a new company called SlingShot. Our goal is to make frequent flyer travel dead simple. We're committed to helping people go further (and more frequently) through the use of responsible personal finance; come see us for your very own frequent flyer plan. 

Below, I share some tips that have helped me see more of the world. These will help you optimize your use of miles, and send you on that next flight for free:

Set a travel goal.

Where do you want to go on your next trip? Having a destination in mind will help you determine which card would be a good fit. Knowing roughly how many miles required for a round-trip ticket is a good place to start:

  • Domestic U.S. Flights: 25,000

  • Caribbean & Central America: 30-35,000

  • South America: 40-60,000

  • Europe: 60,000

  • Asia & Oceania: 70-80,000

  • Africa & Middle East: 80,000

Take advantage of the right offers from Credit Card companies.

Credit card companies want your business, and they earn it by partnering with airlines to give you miles as a signup bonus. As long as you practice responsible personal finance and spend within your means, there is no downside to taking out multiple cards; the average American has 3-5 different cards in their wallet.

Don’t let the minimum spending requirement scare you off.

Many credit cards require you to spend a minimum amount in the first three months in order to earn the bonus offer. While I would never advise taking out a card that requires spending above your means, this article highlights some ways to temporarily boost your monthly spend and receive the value back over time.

Hike to the Top of Offersøykammen | Photo: Matthew Eaton

Avoid flying during peak dates if possible.

Most airlines offer both “Standard” and “Saver” rewards depending on which dates you plan to fly. To get the most out of your miles, try to fly on “Saver” dates. Mild flexibility, as well as avoiding major holidays and peak summer months can make a huge difference towards maximizing your savings. You can refer to Outbound Collective’s excellent and thorough guide for some more tips on which days are typically best to fly.

Know the alliances.

The 60 largest global airlines are divided amongst three major alliance networks: Star Alliance, OneWorld, and SkyTeam. The three largest domestic carriers in the U.S. -- United, American, and Delta -- are split across the three respective alliances. If you happen to live near a hub of one of these airlines, for convenience purposes it may make sense for you to focus your efforts on boosting your mileage on that airline’s corresponding rewards program. For reference on major U.S. hub cities, see below:

United: Chicago, Denver, Los Angeles, Newark, San Francisco and Washington DC

American: Charlotte, Dallas, New York, Miami, Philadelphia, Phoenix and Washington DC

Delta: Atlanta, Boston, Cincinnati, Detroit, Minneapolis, New York, Salt Lake City and Seattle

Likewise, if you find yourself often traveling overseas to the same destination, it may make sense to focus on the alliance that serves your most common route. However, you’ll notice that many larger foreign countries have carriers spread across the three alliances as well.

Star Alliance: Adria, Aegean, Air Canada, Air China, Air India, Air New Zealand, ANA, Asiana Airlines, Austrian, Avianca, Brussels Airlines, Copa, Croatia Airlines, EgyptAir, Ethiopian, Eva Air, LOT, Lufthansa, Scandinavian Airlines, Shenzhen Airlines, Singapore Airlines, South African Airways, Swiss Air, TAP Portugal, Thai Airlines, Turkish Airlines, and United.

OneWorld: Air Berlin, American Airlines, British Airways, Cathay Pacific, Finnair, Iberia, Japan Airlines, LATAM, Malaysia Airlines, Qantas, Qatar Airways, Royal Jordanian, S7 Airways, and Sri Lankan Airlines.

SkyTeam: Aeroflot, Aerolineas Argentinas, AeroMexico, AirEuropa, Air France, Alitalia, China Airlines, China Eastern, China Southern, Czech Airlines, Delta, Garuda Indonesia, Kenya Airways, KLM, Korean Air, Middle East Airlines, Saudia, TAROM, Vietnam Airlines, Xiamen Air.

Capture the Sunset from Mt. Laozhai | Photo: Kyle Obermann

Hopefully this guide will make you feel a bit less intimidated by the frequent flyer system. If you’d like more help, come check us out over at SlingShot for a free, step-by-step frequent flyer plan.

I'm confident in my belief that travel, and the increased understanding across cultures it develops, can pave the way to a more inclusive, connected and peaceful world. Utilizing frequent flyer miles to lower the financial burden is a great place to start.

Happy Travels! Bon Voyage! Que le vaya bien!

Cover photo: Christin Healey

Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph.