The Latest in Travel Hacking

In what now feels like a previous life, I used to travel around the world almost every month. I slowed down a bit two years before the pandemic started, but I still took time for an international trip every six weeks at most.

I was also involved in the early days of the “travel hacking” world. I founded a service, the Travel Hacking Cartel, that served 12,000 members over nearly a decade. I also blogged regularly about credit card deals and other interesting opportunities: getting a hair-loss consultation to earn SkyMiles, for example, or spending $8,000 on useless stickers in exchange for 300,000 frequent flyer miles. I don’t do much work in that world any more, but I still benefit from everything I learned and all the mileage balances I accrued over the years.

If you originally found my blog for travel deals, you might miss hearing about them—so I figured I’d pop my head up to do an extended post for those who are interested.

Oh, and if you want to stay current with that world on a more frequent basis, I recommend my friends Gary Leff, who writes the blog View from the Wing, and Ben Schlappig, who writes One Mile at a Time. Gary and Ben have both been blogging daily (often several posts a day!) for as long as I can remember, and I still read almost everything they write.

Use Card Signups to Earn Points

One of the easiest ways to earn lots of miles and points—which you can then use for lots of free trips—is to sign up for travel rewards cards. You should only do this if you can pay off whatever you spend each month. If that’s you, you likely have the chance to earn many hundreds of thousands of points over time.

Signing up for rewards cards is one of the primary ways I was able to travel to every country (and take many, many other trips as well). Once, I even applied for every card I could find on a single day. Not to fear, however—even if you just get a couple of cards, you can find a lot of value.

The Best Current Offers

Chase Sapphire Preferred – A few years ago I held a meetup at a bar and the server asked me about this card, because so many readers were paying with it. Nearly a decade after its debut, it’s still pretty much the best overall card and most basic starting point for travel hacking. You’ll earn 100,000 Ultimate Rewards points after spending $4,000, which can be transferred to airlines or hotels. If you don’t want to transfer the points, you can simply redeem them as cash credit towards any travel booked through Chase. 100,000 points gets you $1,250 in travel credit. All that for a $95 annual fee! Apply here.

Chase Ink Plus – The business version of the Sapphire Preferred, which offers another 100,000 points (yes, you can get both). It also offers 3x points earning in a number of business categories, as well as cell phone protection for the next time you drop your phone in the bathtub. This one has a higher minimum spend ($15,000 vs. $4,000), so only apply for it if you’re sure you can meet it to get the points. Apply here.

American Express Platinum – Yet another 100,000 points bonus, this one for Membership Rewards points, which can also be transferred to airline and hotel partners. Note that this card has a hefty annual fee ($695), which they’ve been offsetting with various credits. You get $200/year with Uber, $200/year with your choice of airline, $200 in hotel credit, $240 in “digital entertainment” credit, and the list goes on. It can absolutely be worth it if you make sure to use the credits. I’ve had mine for at least a decade. Apply here.

World of Hyatt – Hyatt is my favorite hotel chain, and I’ve had the highest status with them (currently called Globalist) for as long as I can remember. This card comes with an initial bonus of 30,000 points and an additional 30,000 after more spending. It allows you to earn status and free nights through spending, which is rare. You’ll get a free night’s stay every year just for keeping the card, and if you spend more, you’ll get more of them. Apply here.

Marriott Bonvoy American Express – When I’m not staying with Hyatt, I’m usually at a Marriott. This card gets you 150,000 points and an extra Free Night Award after you spend $5,000 in the first three months of having the card. Marriott points aren’t worth as much as Hyatt points to me, but of course 150,000 is a lot of points—so at that level, it’s definitely worth it. Apply here.

Alaska Airlines Visa Business – During the pandemic, I’ve flown Alaska much more than any other airline. This business card gives you 60,000 miles after spending $3,000. The best part isn’t the points, though: it also gives you Alaska’s famous “companion fare” deal, where every year you can take someone with you on a trip for just $99 + taxes. Note that this is the Business version of the card. There are also Personal versions, and you can apply for both. Apply here.

Delta SkyMiles Platinum Card – Similar to the Hyatt card, Delta’s Platinum card allows you to earn qualifying miles for your purchases—not just points you can redeem, but points that help you earn elite status every year. Right now there’s a deal offering 90,000 miles after spending $3,000. At a valuation of $0.01 per point, that’s like getting $900 to spend on flights. Apply here.

Note: In the blog version of this post, there are links to several other cards.

There are many others—take a look through the listings here. I have many of these cards myself. I once had more than 30 active travel rewards cards. I’ve pared down and don’t apply for as many these days, but whenever there’s a good offer, I definitely still sign up!

What Can You Do Besides “Get Credit Cards”?

If you don’t like credit cards or aren’t eligible for some of the most lucrative ones, there are still a lot of things you can do to jump into travel hacking and have significantly better experiences on your next trip. For example:

1. Earning (and keeping) elite status with airlines and hotels helps a lot. It can get you upgraded on flights (despite what you’ve heard, “dressing nice and asking politely” doesn’t work), grant you access to fancy lounges, and provide you better rooms at hotels. Not only that, but whenever something goes wrong, elites are prioritized over peasants non-elite travelers.

Now you might be saying, “Okay, that’s cool, but I don’t fly 80,000 miles or stay in hotels 100 nights a year.” No problem! Status is often given away through various promotions, and you can use one status to “match” to another. It’s magical, and this site shows you exactly how to do it.

2. Next, it’s still possible to buy Round-the-World plane tickets for lower pricing than you’d pay for a number of individual tickets. I used to do this several times a year. (The main challenge now, of course, is that many parts of the world remain closed. But hopefully not for long!)

3. Once in a while an awesome mistake fare pops up where someone at an airline incorrectly prices a route for much less than they intended. Some airlines are better than others about honoring these mistakes, so don’t make any non-refundable reservations for a few days after buying a mistake fare.

4. Airlines will happily sell you miles, and most of the time it’s not a good deal. A few times a year, however, they put them on sale, and buying miles at a discount can work in your favor. Of course, free miles and points are better than cheap miles and points—but the point is, sometimes this is helpful.

5. The world of manufactured spend (MS) or “churning” is a sub-industry of its own. With manufactured spend, you’re trying to put charges on your rewards cards without spending any real money (or at least, by spending very little). Check out this subreddit with more than 350,000 followers for tips and current opportunities. This opportunity is fully worldwide!

These are just a few examples of things that have been around for a long time and probably aren’t going away anytime soon.

Opportunities Change, Be Smart

Travel hacking is a lot like the entrepreneurial model I talk about every day on Side Hustle School: the specific opportunities change over time, but by learning some general principles, you can easily adapt.

If you’re reading this post at some point in the future and one of the offers is no longer available, well, that’s just how it works. Most likely, there will be something new!

I’m traveling again a bit more and am planning my first Round-the-World trip in two years. It will be somewhat limited this time—sadly, my favorite country of Australia has decided to not let anyone in or out for a while—but I look forward to visiting Sri Lanka, Bangkok, London, and Budapest to start.

I’d also love to do more meetups, wherever it’s safe to do so. I’ll post about those on Twitter and Instagram whenever I plan one.

Hope to see you on the road—sometime, somewhere!

P.S. Speaking of free travel, one of my podcast listeners in the UK won a year’s worth of free Airbnb stays! Follow his journey here.

P.P.S. If you like the idea of getting into travel hacking but don’t want to dive into a ton of details, just go here and apply for the Chase Sapphire Preferred card at the top. You can’t go wrong with that one! It will give you $1,250 in value in exchange for a $95 annual fee.


Images: 1, 2, 3, 4

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