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Interview with Tim Winship on Frequent Flier Miles

Tim Winship with laptop, airline royalty program guru, image
Photo caption
Tim Winship monitors miles.

Tim Winship earned his wings by managing airline loyalty programs for more than 20 years. Now he shares his wisdom with fellow miles junkies in his opinionated weekly newsletter, The FrequentFlier Crier (

Q: Is it a good idea to sign up for all the different mileage clubs?

A: The problem is that you end up with miles scattered among different programs, and they're useless until you reach an award threshold. If you'd earned all those miles in a single program, you'd have a free ticket.

Q: Which programs are best?

A: The program with the longest list of partners—other airlines, hotels, rental car agencies—is American's AAdvantage. That translates into real benefits because you have more opportunities to earn miles. But the one with fewest restrictions is Southwest's. One of their selling points is that when it comes time to redeem, you will get a seat if they have one available. But the best program is the one that will earn you the most miles based on your actual travel patterns. Think about your own travel first.

Q: Which are the worst?

A: None of the programs are perfect, but competition being what it is, it's almost impossible for a program to be a total dog.

Q: What's the most common complaint?

A: It's difficult to get an award ticket on the day or to the destination that's your first choice. Airlines are cutting capacity, which means there are fewer seats you can get by redeeming your miles. And programs have continued to add partners, so people are earning more miles. There's a disconnect between supply and demand.

Q: What can people do to increase their odds of getting the ticket they want?

A: Book early—as in 330 days out—or book late. If a flight isn't sold out, airlines often make additional seats available for award travel. Also, be a contrarian. Don't try to get to Honolulu during Christmas vacation.

Q: Should people be charging major expenses on a credit card just to rack up miles?

A: Assuming you get a card with a reasonable APR, and you're paying off all or most of what's due at the end of every month, then it would be silly not to take advantage of some kind of rebate. It makes sense to get something in return for using your credit card.

Q: Are frequent flier programs harder to benefit from now, since airlines are cutting back?

A: Ticket prices are on the decline, so those miles you've been earning are worth less today than they were back when ticket prices were higher. People bend over backward to pad their mileage accounts, then finally get the award and cash it in for a ticket they could've purchased for $100. I see it all the time.

Q: Airline bankruptcies: Hang in or cash out?

A: If you're concerned that the airline is not only going to go bankrupt, but is going to liquidate, then redeem those miles for a ticket. There are other options, like, which allows you to transfer miles or points from one program to another. It's a great concept, but once the conversion is complete, you'll be left with far fewer miles. The only sure way of getting full value for your miles is to redeem them for a ticket.

Photography by David Zaitz

This article was first published in March 2003. Some facts may have aged gracelessly. Please call ahead to verify information.