3 Lessons From Travel Reward Gurus

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Last month, there was a secretive convention of unconventional travel experts. Here's what you can learn from these eccentric folks.

For just the second time ever, the greatest reward travel bloggers, travel hackers, and the savviest business travelers got together in Chicago to share their secrets. It’s a semi-hush-hush seminar called Chicago DO – as in, “Let’s do Chicago” – and it concluded just a couple of weeks ago.

As a travel expert and a long-time follower of some of these hardcore reward travel writers, I was excited to attend last month. I met the people behind all of the tips and tricks I’ve come to admire (and write about here at Money Talks News).  At the end of a long weekend analyzing the hidden benefits of credit cards and travel reward programs, I was able to sum up a few broad lessons that can apply not just to travel hacking, but maybe to some of our other interactions as consumers…

1. Be super nice

You have to be a little nerdy to spend all day studying the terms and conditions of various loyalty programs, and you might even be a little greedy for wanting to travel in first class for free. Nevertheless, the top reward travel experts had one thing in common: They’re all extremely courteous to others.

It may be that they’re just nice people, but they’ve also learned that their friendliness is constantly rewarded. For example, I had lunch with Chicago DO participant David Phillips, a guy who ordered pudding by the truckload when the producer was giving out more miles than the product was worth. Phillips went out of his way to be nice to the company offering the deal, and then donated all of the food to the Salvation Army.

And the participants of this conference raised more than $5,000 for several worthy causes while one of their online forums set a record for charitable lending at Kiva.org. The lesson here: Being nice doesn’t cost anything, but the karma it returns might be valuable someday.

2. Look for weird opportunities to earn points and miles

If you can earn miles from pudding, you can earn them anywhere. Credit cards, rental cars, restaurants, and online shopping portals are just a few of the many places that travel sleuths look to pick up extra points toward free travel.

But can you come out ahead by paying for a flight just to get the miles? Amazingly, yes. For example…

Imagine you’re one flight away from making premier status on your airline, which gets you upgraded to first class on nearly all your flights for the next 15 months.  But to get that status, you need to complete those flights before the end of the calendar year. So you pay $200 for a quick round trip to some place you don’t have any interest in visiting and come home the same day – sometimes never leaving the airport. For $200 and an afternoon flying, you’ve got first class for free for more than a year. Why go through this ordeal? Because only flown tickets count, so you can’t just buy the seat and not show.

There are other scenarios. Like trying to find mistakes in fares offered online and booking them on purpose. If the mistaken fare is lower than the cost of the miles you’d rack up, you do the same thing as above: fly for the heck of it. A few years ago, USA Today described just how many mistaken fares there are.

One Chicago DO speaker even told of paying college students to fly for him, so long as he could use the miles they earned. The only limits to these strategies are the program terms and your own creativity.

3. Use your miles and points wisely

When it comes to award travel, earning points and miles is only half the battle. Finding valuable and creative ways to spend your points is the real challenge.

For example, if you had 50,000 points in American Express’ Membership Rewards program, you could redeem them for the equivalent miles on Delta Airlines and earn a domestic first class ticket. But if you think like a travel rewards guru, you’d find that you could transfer your points to the Flying Blue program run by Air France and KLM, since they’re offering round trip tickets to Europe from several U.S. cities in business class for the same number of miles. Furthermore, this award will take you as far as Tel Aviv, Israel, since their award chart includes it as part of Europe, while other airlines consider it part of the Middle East.

There’s a wild community out there full of people who will do almost anything to travel in luxury for nearly nothing. After meeting many of them, I learned that they represent a broad spectrum of ages, ethnicities, and income levels, yet they were united by their love of finding deals and experiencing new places. I found these people to be not crazy, just very smart and super friendly. I guess traveling around the world in first class can put a permanent smile on your face.

For some other travel secrets that I’ve learned, check out the following posts:

Stacy Johnson

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