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Writer Ethan Steinberg wearing a white medical school coat standing with the ocean and skyline in the background at dusk.

The author, Ethan Steinberg.

Ethan Steinberg



  • As a med school student, I have precious little time off, and my dates aren’t flexible, so booking award travel is challenging.
  • I couldn’t find available award flights to Vietnam for winter break, so I redeemed flexible credit card points for cash flights instead.
  • Even though I spent more points than I would have liked, I don’t regret using my rewards this way.

It feels like much of society is returning to normal after several challenging years of pandemic life, but the travel experience is markedly different. Sure, most countries have reopened their borders and the testing requirements are getting progressively more relaxed, but the actual act of booking your vacation is definitely not the same.

The combination of pent-up travel demand and fewer flights and connecting options, especially for travel to Asia, is making it harder to find premium cabin award space than at any point in the seven years that I’ve been collecting credit card points and miles.

To make matters even more complicated, after several years of traveling full time I just started medical school. My winter break has clearly defined start and end dates, bookmarked on either end by immovable exams and unmissable lectures. Oh, and those late December dates overlap with some of the year’s busiest travel days.

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Here’s why I’m OK with using more credit card points than usual to fit a trip to Vietnam into my limited winter break.

The best value redemption is the one you actually book

With my fiancée set to wrap up a scuba dive master training program in Indonesia at the start of December, I couldn’t miss the opportunity to fly out and meet her in Southeast Asia. We settled on a two-week trip to Vietnam, a destination we’ve both been dreaming of ever since our trip in the fall of 2019 got canceled by a typhoon.

Our home airport of Miami doesn’t have any non-stop flights to Asia, so I knew I was looking at two stops minimum to get to Vietnam; three stops once we decided to start our trip around Da Nang as opposed to Hanoi or Ho Chi Minh city. But I’m not losing sleep over paying twice what I would’ve liked to for the routing we settled on.

Going straight from a cardiology exam to the airport is going to be stressful enough, and while I miss being on the road, I don’t necessarily miss 40-hour-long travel “days.” With less than two weeks on the ground after accounting for travel time, I wanted a lie-flat seat so I could arrive well-rested and enjoy this vacation as much as possible.

Unfortunately, I couldn’t find a single saver-level business class award seat on any airline despite hours of searching and getting very creative with the routing options I considered. I knew I was in trouble when I seriously considered paying 180,000 United miles for a one-way, three-stop Polaris business class routing. Here’s what I ended up booking instead:

  • Miami to Los Angeles in Jet Blue Mint for 72,000 JetBlue points (which I thankfully had lying around from my old Brex Card welcome bonus)
  • Los Angeles to Tokyo to Hanoi in Japan Airlines business class for ~$3,000, which I paid for with 150,000 Chase Ultimate Rewards® points earned from spending on my Chase Sapphire Reserve® and Chase Freedom Unlimited® and a little over $700 cash (since this is a cash fare I’m crediting it to my American Airlines AAdvantage account, earning 9,700 AA miles in the process)

To get home, I booked my fiancée and myself in EVA Air business class from Hanoi to New York-JFK via Taipei. EVA is one of my all-time favorite airlines, so stay tuned for a full review of the inflight experience coming in January. I paid $5,476 for the two of us, and charged it to my Capital One Venture Rewards Credit Card earning 10,952 miles (unfortunately, this fare was only available for booking directly through EVA; if I’d been able to book through Capital One Travel I would’ve earned 5x miles, or 27,380, instead of just 2x).

Capital One Venture Rewards Credit Card


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75,000 miles after spending $4,000 on purchases within 3 months from account opening


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Capital One Capital One Venture Rewards Credit Card

Capital One Venture Rewards Credit Card


Intro offer

75,000 miles after spending $4,000 on purchases within 3 months from account opening


Rewards

Earn 5X miles on hotels and rental cars booked through Capital One Travel. Earn unlimited 2X miles on every purchase.


Rewards

Earn 5X miles on hotels and rental cars booked through Capital One Travel. Earn unlimited 2X miles on every purchase.


Intro offer

75,000 miles after spending $4,000 on purchases within 3 months from account opening


Recommended Credit

Good to Excellent


Regular APR

18.99% – 26.99% Variable

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Chevron icon It indicates an expandable section or menu, or sometimes previous / next navigation options.

Chevron icon It indicates an expandable section or menu, or sometimes previous / next navigation options.

I credited this flight to my United account, meaning I’ll earn about 11,000 miles on this trip. The reason I chose to use my Capital One Venture Rewards Credit Card instead of a card with higher earnings on travel purchases, like my Chase Sapphire Reserve®, is that I was able to redeem my Capital One miles at a rate of 1 cent each to erase this travel purchase from my statement. I have 90 days from the date of the purchase to decide how many miles I’ll redeem versus how many I’ll save for future travel, but I should be able to wipe off at least $4,000 worth of this charge by redeeming 400,000 Capital One miles. 

I’m beyond excited about this trip, but this is most certainly not an aspirational redemption. Not only will I end up paying at least $2,000 out of pocket, but I’m also redeeming about 600,000 miles for the equivalent of three one-way business class tickets between the US and Asia, or a rate of about 200,000 miles per ticket, and that’s not even counting my splurge on the JetBlue Mint flight to LAX. In an ideal world, I’d be looking to pay 100,000 miles or less for these flights, as plenty of programs like Avianca LifeMiles offer one-way saver awards between the US and Asia for those rates. 

At this point, you may be wondering why I’ve gone out of my way to describe in detail an objectively mediocre redemption. I’ve said it before and I’ll say it again, but the best value redemption is the one you actually book. Of course, it’s not a good idea to just carelessly waste your points and miles, but you should also use them happily when they work best for you, instead of comparing your trips to the ones other people take.

With no flexibility on my dates or destination, and no premium cabin award seats available at the time that I booked, something had to give. I opted to prioritize comfort and efficiency, and that meant paying more than I would’ve liked to. I’m incredibly fortunate that after a year of basically no air travel, I had enough points saved up to wipe about $6,000 off the cost of this trip.

Bottom line

Winter break is still a few months away, but if you haven’t started making vacation plans yet you may be surprised at how little award availability is left. Hopefully, if you’re flexible with your dates or destination you’ll be able to find a good value redemption that works for you, but if not, it might be worth looking for cheap cash fares and paying with points.

Many of the most popular transferable points programs, like Chase Ultimate Rewards, Capital One, and American Express Membership Rewards can also be used to cover the cost of cash flights, either by booking through the issuer’s travel portal or redeeming your points to wipe charges off your statement. Not having to compete for limited award space may be the best way to get your vacation planning off the ground. 

We’re focused here on the rewards and perks that come with each card. These cards won’t be worth it if you’re paying interest or late fees. When using a credit card, it’s important to pay your balance in full each month, make payments on time, and only spend what you can afford to pay.



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