Every once in a while I like to look back on some of the amazing things that I’ve been able to do with points and miles. When I first started this hobby, I didn’t open the throttle all that wide. We accrued miles and points, but it took a little while to get comfortable picking up multiple credit cards per year. With a limited stash, shelling out extra miles for business class was crazy talk. Simply flying across an ocean for next to nothing was cool enough.

But things have changed, and my redemption skills have gotten much savvier (and aspirational) over the years. Business class is now much more within reach, as the miles stockpile has grown tremendously. Economy is still the MO, but I’ll splurge now and then. But sometimes even the perfect economy redemption is a phenomenal value. Here are my 5 favorite flight award bookings I’ve made:

United Polaris / 757 Premium Service Across the U.S.

This was a trip planned on a whim, to both see how easy/possible it is to book a premium transcontinental United flight with Turkish Airlines Miles & Smiles and to simply enjoy a day of flying. I even scored a Polaris seat across the country on United’s flagship 777-300ER.

A ticket that would have cost $2,405 for just 25,000 miles and $11.20? That’s value. A massive 9.5 cents per mile of value. Definitely my best airline redemption to date (not that I would ever pay anything close to that for that flight).

a seat on a plane

United First / Asiana Business to Australia

My first premium cabin redemption in early 2017 was a milestone. After flying to/from Europe in 2016, I finally thought about the utility of flying business class, as it would have been a much better experience. The tail end of our outbound itinerary to the French Riviera was miserable.

When United decided that they would be retiring their 747-400s, I jumped at the opportunity to fly Global First (newly rebranded as Polaris First) from SFO to Seoul, followed by Asiana business class to Sydney. The way the award zones worked at the time, this was available for just 80,000 United miles. It was a lot of firsts: first time in first class, first time in true international business class, and first time on an A380. This alone made the solo adventure extremely memorable.

Hawaii for Just 7,500 Miles

This was a relatively recent option made possible by Turkish Airlines’ extremely attractive domestic pricing. Because domestic applies to everywhere within the U.S., not just the lower 48, you can book a ticket to Hawaii for just 7,500 miles in economy or 12,500 in first/business. So this is exactly what I did for just a couple nights.

Cathay Premium Economy and Business With Hong Kong Stopover

Here I put Alaska’s amazing one-way stopover rules to good use by booking a one-way flight home from Beijing with a stop in Hong Kong. This let my older two kids and I visit two Chinese cities for the price of one. We even got to fly both the business and premium economy cabins on one of Cathay Pacific’s 777 aircraft.

I don’t know the actual value of the ticket, but it was excellent, given that we paid just 50,000 Alaska miles per person for our itinerary.

a plane parked on the tarmac

The “One Way” Pen Air Round-Trip to Portland

This makes the list since it is one of the “hackiest” awards I’ve ever booked. For a brief period, PenAir served our tiny airport from Portland, Oregon, flying the ACV-PDX hop using Saab 340 aircraft. While flying such a small plane was cool enough by itself, booking a “one-way” ticket for just 7,500 miles to fly it was even cooler. We met family for a long weekend in Portland, and definitely did so on the cheap.

It was an interesting use of Alaska miles. Rather than booking ACV-PDX-ACV for 15,000 miles round-trip, I booked ACV-PDX (stopover)-OAK for just 7,500 miles one-way, per person. Cash tickets in either case were about $280 round-trip.

Sure, we’d land 5 hours from home, but given that my in-laws had booked their tickets out of STS, just over an hour from Oakland, it was easy enough to fly to the East Bay, catch transportation up to Sonoma County, and all go home together. It was a happy savings of 15,000 valuable Alaska miles.


While my metrics include more than just the cents-per-point “value” of the award, these are definitely my top five favorites over the years. Now your turn: what are YOUR best award redemptions ever made?