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How Do I Figure out Which Award Redemption Is Best?

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TPG reader Jenn tweeted to ask about strategies for booking award travel:

“@ThePointsGuy — With so many ways to book award travel, how do we figure out the best option once we decide to go to somewhere?”

Like revenue travel, I find that most award bookings are a trade-off of convenience, comfort and cost. Sometimes you get lucky and nail all three, but usually you’ll have to sacrifice a bit of one for the sake of another.

When I’m booking an award, I first look at routings and flight schedules. Generally, I’d rather take a nonstop flight and avoid a super early departure time even if it means spending a few more miles. However, a long layover or stopover can actually make your trip more memorable, especially in a cool city you’ve never been to before. You’ll have plenty of airlines to choose from when you’re traveling to popular destinations, but you can narrow your search by eliminating any flights that clearly don’t mesh with your plans.

Next, I look at the quality of the options available. I’m usually willing to be flexible about my schedule in order to fly in a premium cabin, partly because I’m tall, but also because some first and business-class seats truly enhance the experience. This is mostly true of longer international flights, but some domestic transcon service is worth paying extra for as well. If you’re just taking a short flight home for the holidays, there’s no need to make a splash. However, if you’re planning a vacation to remember, you might as well go big. You can always earn more rewards, but you can never get back the 14 hours you spent scrunched into a middle seat in economy.

I find a first-class seat is well worth the extra cost on longer flights.

Finally, I consider the value of each award redemption. While you can often get the exact flight you want if you’re willing to cough up enough miles, it’s worth being flexible if it means you can redeem at the saver level. I know I just said you can always get more rewards, but that’s no reason to burn them needlessly! Use my monthly valuations to help you figure out whether a given redemption is worthwhile. If you’re in that ballpark, then you’re doing fine.

Of course, any of these factors could be more important or totally inconsequential to you than the others. If you’re working with limited resources, for example, then you might forego comfort and convenience and just look for whatever flight will get you from A to B at the lowest cost. Or, maybe you want to try the Etihad A380 first-class Apartment and you’re not worried about the flight times or mileage requirements. Value is in the eye of the redeemer, and if you’re happy with what you get, that’s what matters.

Ultimately, the best redemption is the one that meets your needs, whatever those may be. Unless, of course, you’re redeeming for merchandise. In that case, we might need an intervention!

If you have any other questions, please tweet me @thepointsguy, message me on Facebook or send me an email at

Chase Sapphire Preferred® Card

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  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Earn 5,000 bonus points after you add the first authorized user and make a purchase in the first 3 months from account opening
  • No foreign transaction fees
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel
  • No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards
Intro APR Regular APR Annual Fee Foreign Transaction Fee Credit Rating
N/A 16.24%-23.24% Variable Introductory Annual Fee of $0 the first year, then $95 0% Excellent Credit