Travel Hacking: Unlock Free Flights & First Class Upgrades | [Your Brand]

A few years ago, I flew my family of four from Portland, Maine to San Antonio, Texas for a family wedding—for free.

Had I paid for the airfare, the cost would have rung up at over $2,000.

Also awesome: I’ve gotten free first-class upgrades on about six out of the last 10 flights I’ve taken, even though I usually buy the cheapest ticket available.

Relative to consultants and sales reps who are on the road every week, I’m not a frequent traveler. I might fly four or five times a year to conferences for work.

But I still leverage travel points to get free trips and an upgraded travel experience.

If you’re not collecting travel points, this is why you should start.

This post will give you an introduction to travel hacking. We’ll start with basic things anyone can (and should) do to save money on flights. Then we’ll progress to the ways I racked up close to a million Delta SkyMiles while still in my 20s.

How to start travel hacking (Level 1): Get the best deal on every flight

Most of you aren’t living under a rock, so I don’t need to tell you that you should start your search for a flight with a site like Kayak that searches multiple travel sites for the best fares, or even Expedia or TripAdvisor. Skyscanner or Momondo are good for foreign routes.

Be as flexible as possible: If you search for alternate airports and dates to avoid peak business travel times, you can save hundreds of dollars. Priceline is still the best way to score unpublished fares and hotel rooms if you can be as flexible as possible.

But here are some things you might not know:

If you’re traveling on an international airline, go to the airline’s foreign website to see if the airfare is cheaper in another currency

For example, search airfrance.fr instead of airfrance.com. You’ll have to do some conversions, and also consider whether your credit card will charge you a foreign transaction fee. (Here are some travel cards that don’t.)

Check your destination airport to see all the airlines that fly there.

There may be some smaller airlines that cost less but don’t show up in the aggregator sites. For example, if you’re flying from New York to Continental Europe, it may cost less to fly to London and then switch to a low-fare airline to hop from London to your destination city. (But you may have to book the tickets separately.)

Call a travel agent that specializes in your destination.

Once I traveled to Croatia, Bosnia, and Herzegovina. We used a Croatian travel agency in New York that arranged a multi-stop air itinerary on different airlines that came to about $1,500 per person, which was half what we were finding on our own. Travel agents may not always be less expensive, but they’re worth a shot.

How to start travel hacking (Level 2): Collect and use frequent flyer miles

This is where it gets fun.

By travel hacker standards, my system is simple: Years ago I picked an airline (Delta) that I liked to fly and that offered a good amount of routes from my city. I became loyal, choosing to fly Delta whenever possible, even if the ticket was ~$50 more than a competitor.

At the same time, I got Delta’s affinity credit card—the Delta SkyMiles Card from American Express. Right off the bat, signing up got me bonus miles worth almost enough for a free flight, and the card comes with other perks, like free checked bags and double miles on the airfare I book.

Many of these travel rewards credit cards come with free points to get you started.

Now, for someone who can’t commit to airline loyalty, airline credit cards aren’t the best deal. Generic travel rewards credit cards offer more rewards per dollar spent, and the airline cards have annual fees and higher-than-average interest rates, which is why you should never, ever use these cards if you can’t pay the balance in full each month. 

What these cards are great for, however, is accelerating how many points you can earn each year. The Platinum version of Delta’s card, for example, gives you a 10,000-mile bonus when you hit a certain spending threshold.

If you fly enough each year on one airline, you can obtain elite status. Although there are other perks that come with “status,” as it’s known in frequent-flyer lingo, by far the most coveted is the complimentary first-class upgrade.

How travel hackers get first-class upgrades for free

Here’s how it works. Very few people pay out of pocket for a pricey first-class ticket. In the last few days or hours before a flight takes off, the airline begins awarding unsold first-class seats to passengers with elite status. Each airline has several tiers of status, so the passengers who fly the most get first dibs and it trickles down. Other factors, like weather delays and how much you paid for your ticket, might bump a lowlier elite flyer to the top of the list.

It’s luck of the draw, but I’ve gotten first-class upgrades on 50%-60% of my Delta flights—including some long hauls from Las Vegas to Boston—since I became a Silver Medallion member three years ago.

Admittedly, my success ratio for scoring upgrades fell after Delta merged with Northwest, because the number of elite flyers on the combined mega-airline shot up. If I can fly enough this year, combined with the qualification miles the Delta Amex will earn me, I may be able to reach Gold level next year.

How to get your first free flight

If you have good credit and no debt, the best place to start is with an airline credit card’s sign-up bonus. Here’s a list of some of the available bonuses right now. Many will get you enough points for your first free flight (or very, very close).

Many people are concerned that signing up for new credit cards will hurt your credit score.

This may be true if you have a lot of credit card debt already, but if you’re relatively debt-free and have good credit, applying for a few new cards won’t hurt as long as, you know, you don’t go crazy and max them out! What you want to avoid, however, is opening them, grabbing the bonus, and then closing them, a process known as “churning.”

Bottom line: Only get cards that you’re comfortable keeping for a few years.

Enrolling in miles programs

If you’re not in a position to sign up for a card, at least sign up for a few frequent travel rewards programs (airlines and hotels)—even if you’re not traveling anytime soon.

Here are some of the biggest to get you started:

• Air Canada Aeroplan
• American Airlines AAdvantage
• Delta SkyMiles
• Frontier Airlines EarlyReturns
• JetBlue TrueBlue
• Southwest Airlines Rapid Rewards
• United Airlines MileagePlus
• U.S. Airways Dividend Miles

And hotels:

• Hilton HHonors
• Hyatt Gold Passport
• InterContinental (Holiday Inn) Priority Club Rewards
• Marriott Rewards
• Radisson Gold Rewards
• Starwood Preferred Guest
• Wyndham Rewards

Most rewards systems have ways to earn points other than traveling. For example, I’ll get emails from Delta offering points for completing surveys or purchasing something through their link. (Around holidays they send out miles deals for FTD Florist, so I can pick up a few miles by sending my wife flowers, which I would probably do, anyway).

Once you’re a member of a few rewards programs, use them! Any time you fly or stay at a hotel, make sure you use your number. Some hotel chains, for example, allow you to “double dip,” meaning you can apply both your hotel rewards number and an airline program to your stay, earning both points and miles.

Buying or challenging for status

If the thought of free first-class upgrades has you jittery, you can get there faster. If you have the cash, U.S. Airways lets you buy status outright. Other airlines let you get there faster by taking a “points challenge.”

Basically, you have to call up the airline (they don’t advertise this) and tell them you’re a frequent flyer and want to take a points challenge to earn status. It works best if you hint that you’re loyal to another airline and want to switch.

There may be a fee to take the challenge, and then you have to earn a certain number of miles within a limited time frame, say 90 days.

On American Airlines, you can challenge for Gold or Platinum status by calling 1-800-882-8880 and paying a fee of $120 or $240, respectively. To get Gold status, you must earn 5,000 Elite Qualifying Points (EQPs) in 90 days, and to get Platinum you must earn 10,000 EQPs in 90 days. Ordinarily, you have to earn 25,000 or 50,000 EQPs over the course of a year.

Buying status isn’t cheap. American Airlines discounts the EQPs you earn on cheap tickets, so you’ll have to fly more miles or buy higher-cost tickets to meet the challenge thresholds. But if you fly often, it pays for itself in future upgrades (if you consider the money saved over paying first-class fares).

Maximizing your rewards

You can only collect points so fast—you’ll need to travel a bit to accumulate much of a balance. Credit card bonuses are obviously the fastest way to accelerate this.

But the real art of travel hacking is not in collecting points, but in redeeming them.

Most of the time, a single airline mile is worth somewhere between $0.01 and $0.02. It all depends on how you spend it.

You might, for example, redeem 50,000 miles for a round-trip domestic ticket that costs $300. That’s a per-mile value of just six-tenths of a penny. Not good.

Let’s say, however, that you save up 200,000 miles and redeem it for a business-class international ticket that sells for $8,000 (crazy, I know). You’re getting $0.04 per mile.

Obviously, rewards are only good if you can use them—so this won’t always apply. But this is also why it makes sense to focus your efforts (at least in the beginning) on one or two airlines, so you can obtain a critical mass of points more quickly.

Two of our favorite travel cards

Chase Sapphire Preferred® Card is a wonderful example of maximizing your rewards points. Normally, the 60,000 bonus points that you earn when you sign up for this credit card and spend $4,000 within the first three months would be valued at $600. However, when you trade in your points using the Chase Ultimate Rewards® program, you get $750 for the same amount of points.

Some of the major names that work with the Chase Ultimate Rewards program include British Airways, Hyatt, Marriott, Singapore Airlines, IHG, Virgin Atlantic, United Airlines, Southwest Airlines, and Ritz Carlton. And, since you receive the 60,000 bonus points almost immediately after reaching the spend hurdle, you won’t have to wait long to use them for your next flight.

If you can do it responsibly, taking advantage of sign-up bonuses is the way to go when it comes to maximizing your travel rewards potential. The Citi Premier® Card has a generous welcome offer of 80,000 bonus points when you spend $4,000 in the first three months. That translates to a lot of airline or hotel reservations, fast! Or, you can redeem that for $800 in gift cards when redeemed at thankyou.com. 

The Citi Premier® Card also comes with plenty of earning potential in the form of its rewards program. Cardholders can earn 3x points for every dollar spent on air travel, hotels, gas stations, restaurants, and supermarkets, as well as 1x points on all other purchases. Some nice additional travel perks include no foreign transaction fees and a $100 Annual Hotel Savings Benefit after you spend $500 on a hotel stay.

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