Working the Frequent-Flier System

By Michelle Singletary
Sunday, November 4, 2007

I remember sitting in my grandmother's living room, licking S&H Green Stamps and pasting them in prize booklets in hopes of getting something for free.

Funny thing is, I can't recall a single thing we actually got for those stamps -- and for all the gluey taste on my tongue.

Fast forward and the Green Stamps of today are frequent-flier programs or hotel reward points or some loyalty program promising you free airline tickets, hotel stays or car rentals in exchange for your repeat business.

But I often wonder if our loyalty is really worth the aggravation it takes to redeem those miles and points.

I once spent a considerable amount of time trying to redeem miles for two tickets to Hawaii for our 10th wedding anniversary. Now we're about to celebrate our 16th anniversary, and the ticketing ordeal is still fresh in my mind.

I'd found a decent flight outbound but couldn't find any seats for customers like me -- folks redeeming miles -- for the return. There were too many blackout (restricted travel) dates. Finally, I was told that to get a flight home, I would have to relinquish extra miles. In desperation, I relented. Otherwise I would have had to stay an extra week to get a flight that wasn't blacked out.

It's that kind of frequent-flier frustration that led Randy Petersen and Tim Winship to team up to write "Mileage Pro: The Insider's Guide to Frequent Flyer Programs" (OAG Worldwide, $19.95). It's the November pick for the Color of Money Book Club.

For years, "members of frequent-flyer programs have been trying to make sense of these deceptively simple yet endlessly complicated programs," they say.

These two men have made a career out of helping frequent fliers. Petersen publishes InsideFlyer magazine as well as several travel-related Web sites, including and Winship is the publisher of and editor-at-large for

Petersen says that as a former manager for a large menswear retailer, he spent a lot of time flying and keeping track of his mileage awards. He became the go-to guy when friends wanted advice about how to best use their reward programs.

Winship is the insider. He spent 20 years in the travel industry working in loyalty marketing for Singapore Airlines, All Nippon Airways and Hilton Hotels. He developed frequent-flier programs.

The guide these two have put together could be helpful as you begin to plan for a spring break or your summer vacation next year.

"Mileage Pro" is a book many of us need. You have to know how to work the system to "squeeze every ounce of value" out of these membership-has-its privileges programs.

"Many rewards go unredeemed because travelers either do not have the time to use them or have not learned how to manage them," the authors write. "Other travelers do not concentrate their loyalty, finding themselves with miles and points scattered everywhere except in the program from which they are seeking free travel."

The authors believe that if you manage travel-loyalty programs well, you can enjoy some nice perks and minimize the headaches in redeeming your rewards. For example, they point out that more than 50 percent of all miles and points are earned without leaving the ground. Use the right partnerships and you boost your freebies.

Petersen and Winship say it is particularly important to keep track of your points and miles. An estimated 7 to 8 percent of travel is improperly recorded, they point out. That's not a high figure, but you certainly don't want to be cheated out of a single mile or point.

This primer covers quite a lot of ground, including why it's worth trying to gain elite status, how best to exchange miles and points among programs and what strategies to use in converting miles and points into money. In one chapter, the authors compile the 52 best pieces of frequent-flier advice. There is also a useful resources section with travel-related Web sites and publications.

I assure you, this is one book you will want to take with you when you travel. Read it while waiting to board your flight and maybe next time you can enjoy a free ride.

To become a member of the Color of Money Book Club, all you have to do is read the recommended book. I also invite you to join me live online to discuss the books with their authors. This month both Petersen and Winship will be my guests to take your questions about your frequent-flier plan at at noon Eastern Time on Nov. 29.

In addition, every month I randomly select readers to receive copies of the book, donated by the publisher. For a chance to win a copy of "Mileage Pro," send an e-mail to Please include your name and address so we can send you a book if you win.

¿ On the air: Michelle Singletary discusses personal finance Tuesdays on NPR's "Day to Day" program and online at also has a new personal finance call-in show that airs Sundays on XM Satellite Radio, Channel 169 "The Power," at 8 to 10 p.m.

¿ By mail: Readers can write to her at The Washington Post, 1150 15th St. NW, Washington, D.C. 20071.

¿ By

Comments and questions are welcome, but because of the volume of mail, personal responses are not always possible. Please note that comments or questions may be used in a future column, with the writer's name, unless a specific request to do otherwise is indicated.

© 2007 The Washington Post Company