Free Travel: Still Doable, With the Right Loyalty Program

Financial Goals

photo: jpmueller99

If I focus hard enough, I can remember the last time I redeemed 25,000 miles for a free round-tip plane ticket.

But just barely. I think it happened in the 1990’s. Nowadays, the conversation goes like this:

Me: I’d like to redeem my miles for a free ticket.

Airline rep: Sure thing. Would you like to fly the red-eye to Buffalo?

Me: I was thinking more like a daytime flight to JFK.

Airline rep: Ha ha! You are funny.

Tim Winship, founder of, says I’m not the only disappointed travel-deal seeker these days. “Since these programs came into existence in 1981, I would say it’s probably never been more difficult” to make those 25,000-mile redemptions. There are so many blackout dates on the airlines’ calendar, it looks like a declassified CIA document.

Granted, getting a free flight would be a lot easier if you had 50,000 miles to throw around for a non-restricted ticket. But that’s a whole lot of flying and credit card spending to get one lousy round trip.

This is how my wife and I ended up with close to 75,000 Continental OnePass miles, no idea how to use them, and no desire to have another dispiriting conversation with a customer service rep. “It might get better at some point in the future,” says Winship, “but I think with the economy the way it is, it’ll be at least a couple of years before there’s any significant improvement, if there is at all.”

It turns out, though, I’ve been laboring under a total misapprehension about how frequent flyer programs work. I thought if I was loyal to a particular airline, the airline would reward me with upgrades and free tickets on my favorite routes. (I still remember that one blissful year when I qualified for elite status. I didn’t actually get many upgrades, but the card looked good in my wallet.)

That’s how frequent flier programs worked that way in the distant past. Not any more. There are just too many paying customers chasing too few seats, and it looks like only George Clooney is loyal to one airline.

But there are two classes of reward programs that, even today, work exactly like the frequent flyer programs in their glory days: Amtrak and hotel rewards.

Riding the Rails

Fasten your seatbelts now, because I’m about to share a strategy that will save my family exactly $1,005 on our next vacation: Amtrak Guest Rewards.

The railroad company’s rewards program shares points with Continental Airlines (CAL) (which, most of you travel buffs surely know, will merge with United Airlines (UAL) on October 1). Right now, you can transfer an unlimited number of OnePass miles to your Amtrak account and up to 25,000 miles a year from Amtrak to Continental.

And compared to booking airline rewards, using Amtrak points is sweet and buttery. My family was already planning to get a sleeping compartment on the Coast Starlight, Amtrak’s most scenic route, from LA to Seattle next summer. That’s $1,005 retail—or 20,000 points.

We had 20,000 points under our virtual couch cushions and didn’t even know it!

It gets better. We ride Amtrak to Portland or Vancouver at least twice a year. That’s 1,000 points per person each way, or 6,000 points total. At this rate, I’m not sure if we’ll ever pay to ride the train again, unless we ride during one of Amtrak’s few blackout dates (25 days per year).

And now you see the catch: you have to ride Amtrak. Or, as Tim Winship put it, “If you’re an Amtrak customer, then it’s kind of a no-brainer. But my sense from dealing with the people that I deal with—namely, travelers—the Amtrak program isn’t on the radar of a lot of people simply because they’re not train travelers.”

Yes, I know: Amtrak is fraught with infuriating delays, and people who visit the US from other countries find it absurd that we run freight and passenger trains on the same rails.

To which I say: Oh yeah? Once when I was on British Rail, the train was held up by sheep. True story. More to the point, Amtrak is absolutely, hands-down, the best way to travel from Seattle to Portland or Vancouver. Possibly other routes, too. Be sure to check for yourself.

Stay the night

Maybe Amtrak’s not for you. Aren’t there any other loyalty programs that reward your patronage with more of the same rather than a red eye to Sandusky?

Sure. They’re called hotel programs. “Redeeming points for free hotel stays has never been a particular issue,” says Winship. Indeed, the flagship programs like Starwood Preferred Guest (Westin, Sheraton, W, and others) and Hilton HHonors have no blackout dates whatsoever. As long as there’s a room available, you can book it over Thanksgiving. Move up through the elite ranks, and you’ll get free upgrades, breakfast, internet, and a shiny gold or platinum card to replace that formerly glorious elite flyer plastic in your wallet.

Winship also pointed out that if you’re a member of the Starwood program, you can transfer points one-to-one with many frequent flyer programs—plus Amtrak. Since Starwood lets you use its points on multiple airlines with no blackout dates (a $400 ticket, for example, will cost you 30,000 points), you’ll want to transfer in, not out. 

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