3 Lessons From Travel Reward Gurus

Photo (cc) by Drew Coffman

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:

Disclosure: The information you read here is always objective. However, we sometimes receive compensation when you click links within our stories.

Read Next
33 Home Upgrades That Cost Less Than $100
33 Home Upgrades That Cost Less Than $100

A little money goes a long way with these imaginative projects. You can do most of them yourself.

11 Home Upgrades With the Best Payback in 2020
11 Home Upgrades With the Best Payback in 2020

The home remodeling projects that deliver the best bang for the buck tend to have one thing in common.

7 Social Security Blunders That Can Ruin Your Retirement
7 Social Security Blunders That Can Ruin Your Retirement

Making even one of these mistakes can easily cost you tens of thousands of dollars.

7 Secret Departments of Amazon You Should Know About
7 Secret Departments of Amazon You Should Know About

These little-known sections of Amazon are hidden gems for deal-seekers and impulse shoppers alike.

10 Colleges That Offer Free Tuition for Seniors
10 Colleges That Offer Free Tuition for Seniors

These schools let retirement-age students study, tuition-free, while earning college credit.

View this page without ads

Help us produce more money-saving articles and videos by subscribing to a membership.

Get Started

Most Popular
20 Things That Are Actually Worth Stockpiling
20 Things That Are Actually Worth Stockpiling

You don’t need a year’s supply of toilet paper to survive an outbreak, but consider stocking up on these items.

Can a Twice-Divorced Woman Claim Social Security Survivors Benefits?
Can a Twice-Divorced Woman Claim Social Security Survivors Benefits?

Understanding survivors benefits rules is the key to getting the most from your benefit.

9 Things You’ll Never See at Costco Again
9 Things You’ll Never See at Costco Again

The warehouse store offers an enormous selection, but these products aren’t coming back.

These Are the 10 Worst Cars for Depreciation
These Are the 10 Worst Cars for Depreciation

Two types of vehicles are especially likely to see steep plunges in value.

Never Buy These 10 Things With Your Credit Card
Never Buy These 10 Things With Your Credit Card

Credit cards offer many conveniences and protections, but sometimes it’s simply smarter to keep the plastic tucked away.

13 Amazon Purchases That We Are Loving Right Now
13 Amazon Purchases That We Are Loving Right Now

These practical products make everyday life a little easier.

9 Mistakes Everyone Makes When Shopping on Amazon
9 Mistakes Everyone Makes When Shopping on Amazon

Are you losing money due to any of these missteps?

5 Ways Social Security Will Change in 2021
5 Ways Social Security Will Change in 2021

These adjustments will affect both workers and retirees in the new year.

11 ‘Disposable’ Items You Should Be Reusing
8 Things You Should Buy at Restaurant Supply Stores
8 Things You Should Buy at Restaurant Supply Stores

You don’t have to be a chef or a restaurant owner to shop here.

Stop Buying These 19 Things Online
Stop Buying These 19 Things Online

The internet has changed how we shop. But for some things, you’re still better off buying the old-fashioned way.

10 Things I Always Buy at Trader Joe’s
10 Things I Always Buy at Trader Joe’s

From snacks to sweets to side dishes, stock your cart with these time-tested favorites on your next TJ’s run.

19 High-Paying Jobs You Can Get With a 2-Year Degree
19 High-Paying Jobs You Can Get With a 2-Year Degree

There are easy high-paying majors available in the U.S. — and no bachelor’s degree is required. We’re here to help you find easy degrees that pay well.

Cut These 11 Expenses Now If You Hope to Retire Early
Cut These 11 Expenses Now If You Hope to Retire Early

Like the idea of financial independence? Part of the FIRE equation is cutting costs.

3 Ways to Get Microsoft Office for Free
3 Ways to Get Microsoft Office for Free

With a little ingenuity, you can cut Office costs to zero.

7 Tips for Building an Emergency Food Supply
7 Tips for Building an Emergency Food Supply

A pandemic or natural disaster could leave you reliant on your existing emergency food supply. Is your pantry well-prepared for emergencies? Knowing what to stock up on for emergencies can be a difficult task and we’re here to help.

These Are the 4 Best Medicare Advantage Plans for 2020
These Are the 4 Best Medicare Advantage Plans for 2020

Medicare Advantage customers themselves rate these plans highest.

5 Secrets of Seniors Who Keep Their Minds ‘Young’
5 Secrets of Seniors Who Keep Their Minds ‘Young’

Here is why some seniors’ brains work as well as those of people who are decades younger.

11 Things Retirees Should Always Buy at Costco
11 Things Retirees Should Always Buy at Costco

This leader in bulk shopping is a great place to find discounts in the fixed-income years.

View More Articles

View this page without ads

Help us produce more money-saving articles and videos by subscribing to a membership.

Get Started

Add a Comment

Our Policy: We welcome relevant and respectful comments in order to foster healthy and informative discussions. All other comments may be removed. Comments with links are automatically held for moderation.