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The Upgraded Points Team’s Best Redemptions of 2023

Chris Hassan's image
Chris Hassan
Chris Hassan's image

Chris Hassan

Social Media & Brand Manager

Countries Visited: 21U.S. States Visited: 24

Chris holds a B.S. in Hospitality and Tourism Management and managed social media for all Marriott properties in South America, making him a perfect fit for UP and its social media channels. He has a ...
Edited by: Juan Ruiz
Juan Ruiz's image

Juan Ruiz

Compliance Editor & Content Contributor

Countries Visited: 40U.S. States Visited: 27

Juan has been involved in credit cards, loyalty, travel, and personal finance for more than 10 years. He has worked for several outlets including The Points Guy and Forbes and was previously Editor-in...

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We all love a good redemption story, but here at Upgraded Points, that usually has something to do with points and miles.

Whether visiting family or flying across the world to see Taylor Swift perform, our team put together a unique and impressive list of award travel redemptions in 2023.

This list is an excellent example of how it’s not always about getting the best cents per point (CPP), but making your points and miles work for you and your travel goals.

Let’s take a look at where our team decided to earn and burn their points and miles this year.

Alex Miller, Founder & CEO

My recent redemption with British Airways was flying from Houston (IAH) to London (LHR) for a quick trip back home to see the family.

I used my BA companion ticket to fly roundtrip in first class, and that saved me 50% of the Avios normally required. I had used a previous 30% transfer bonus from American Express to BA back in August, which made it even sweeter.

The total was 85k Avios (off-peak) + $2,268.90. It was not the least expensive redemption, but it was less due to the 30% transfer from Amex. Furthermore, I also used my British Airways Visa Signature® Card, so I got $200 back from the taxes and fees, bringing it down to $2,068.90.

Carissa Rawson, Senior Content Contributor

One of the more exciting redemptions I made in 2023 took place just last month. Anyone with an internet connection has likely seen that Taylor Swift’s hugely popular Eras Tour is making its way worldwide.

While I like her music, I’m not a HUGE Swiftie, so paying $3,000 for a ticket to a show in the United States seemed a bit excessive to me. However, another point and miles friend and I started tossing around the idea of traveling to see her concert — and it made sense.

Premium tickets for a show in Brazil topped out at $300 each, even on the resale market, so we made the decision to jump down for 48 hours, get in a swift concert experience (see what I did there?), then make our way back home.

I had an interesting time finding flights down to Rio de Janeiro (GIG). Those who’ve been to South America before know that U.S. airlines tend to charge a lot for these flights and hardly ever release award space. However, after copious amounts of finagling, I snagged myself a one-way flight from Los Angeles (LAX) to Santiago, Chile (SCL) on LATAM in business class for just $1,008.

This was available via and nowhere else, which goes to show that you should ALWAYS search multiple sites for the best prices.

Now that I had determined my way there, I needed to find my way back home. Fortunately, that same LATAM flight had business class award availability on my return — and it’s a great deal when using Alaska miles at 45k miles for business class LATAM flights (it’s going up to 55k soon). It’s not the most premium product in the sky, but with a lie-flat bed and delicious food, I wasn’t complaining.

The round-trip cost for these flights usually hovers in the $4,600 range, so I’m glad to have paid just $1,000 and 45k miles for the experience. Plus, I credited the mileage earned to Alaska Airlines, which tipped me into earning MVP Gold status for the year.

Once in Santiago, I paid cash for a flight over to Rio, which ran just over $300 round-trip. Cash rates for hotels in Rio De Janeiro were exorbitant the weekend we were visiting (thanks, Taylor!), so it made sense for me to redeem points for my stay.

As a Category 4 hotel in the World of Hyatt program, it cost me 24,000 points for a 2-night stay at the Grand Hyatt Rio De Janeiro. I’m a top-tier Globalist with Hyatt, so access to the club lounge and free breakfast made a huge difference in the quality of my stay.

Ocean Lagoon Suite King Bed Grand Hyatt Rio de Janeiro
Ocean Lagoon Suite King Bed at the Grand Hyatt Rio. Image Credit: Chris Hassan

Surprisingly, the only person I knew in Brazil was traveling to Rio to attend the Taylor Swift concert on the same day. You guys have probably heard of him — Chris Hassan, the man behind all of Upgraded Points’ social media. Once we realized we’d be around at the same time, he swapped over to the Hyatt as well so we could all spend some time together.

Hilariously, after all was said and done, the entire concert was canceled and moved to a few days later.

I could have stayed on to see it (Chris and his family did), but after a few days of flying, a great time at the hotel pool, and a wildly sweaty heat wave, I was glad to call it a day and head home.

Was this my best redemption? I’m not sure it counts since I didn’t actually see the show. But I got great value for my points, spent time with friends, and now have a tale to tell about when I flew to Brazil to (almost) see Taylor Swift perform!

Christine Krzyszton, Senior Finance Contributor

One of my favorite redemptions this year was using the fifth-night free benefit on a Marriott Bonvoy points booking. This perk is especially useful in Spain, where there are many AC-branded hotels, of which I am a fan. I’ve utilized the fifth-night free benefit in cities across Spain, including Madrid, Valencia, Malaga, Palma de Mallorca, Alicante, and Almeria.

For example, AC Valencia recently cost me a total of 46,000 points for 5 nights. This is a fantastic value for families, making 2 rooms an affordable option.

Christopher Hassan, Social Media & Brand Manager

Hawaii is always a good idea, especially when you can book with points and miles.

After taking my family to Maui and Oahu for the first time in 2022, I couldn’t shake the urge to get back to the islands in 2023. This time, we wanted to explore the Big Island.

After an obsessive amount of research, I finally decided to book the Hilton Waikoloa Village on Hawaii’s Big Island. This massive property has boats, a monorail, dolphins, waterslides, and more. It’s an ideal hotel for a family vacation.

Hilton Waikoloa Village photoshoot
Hilton Waikoloa Village photoshoot. Image Credit: Chris Hassan

Award rates started at 70,000 Hilton Honors points per night, but with the fifth night free when redeeming points, the total was a very reasonable 280,000 points for our stay. With cash rates reaching over $1,000 per night, this was an absolute steal of a redemption.

Plus, the resort fees were waived since it was an award stay, and as a Hilton Diamond member, we received an upgrade and daily dining credits. To top it off, our incidental charges triggered the resort credit on my Hilton Honors American Express Aspire Card!

Overall, we had a great stay at a beautiful Hawaiian resort for almost no out-of-pocket cash.

Ehsan Haque, Content Contributor

I found some last-minute availability for ANA First Class when searching on the United website between Chicago and Tokyo and decided to take a quick trip to Japan!

ANA First Class Empty Window Seat
Image Credit: Stella Shon

I called up Virgin Atlantic and transferred over points from Chase Ultimate Rewards. Better yet, Chase had a 30% transfer bonus, allowing me to book ANA First Class for just 47,000 miles one-way (this was booked before Virgin’s devaluation of ANA awards).

Since I booked a one-way to Japan, I needed to find an award flight home.

I decided to go big or go home, so I booked Japan Airlines first class as I wanted to see how it would compare to ANA first class. Japan Airlines usually has decent last-minute award space and I was able to find availability relatively easily.

For this part of the redemption, I opted to book this award using 80,000 American AAdvantage miles, saving a significant amount of money considering that this first-class experience normally retails north of $9,000!

Juan Ruiz, Compliance Editor & Content Contributor

This year, I crossed a few things off my bucket list, and I’m proud of them.

From Dubai (DXB) to Washington Dulles (IAD), I was able to book and experience Emirates First Class on the A380 for 136,250 miles and $860. I had to move American Express Membership Rewards to Emirates’ Skywards program because partner miles can no longer be used to book First Class awards.

A380 emirates
Image Credit: Airbus

Even though I had to use loads of points and pay crazy taxes and fees, I wouldn’t have been able to shell out $8,000 in cash for this one-way trip. I got almost 6 cents per point by transferring Amex points to Emirates Skywards for this luxury flight.

Another significant redemption in 2023 was securing award space and booking Etihad’s First Class Apartment on the A380. This premium flying experience has been on my bucket list for years, and now I’ll be able to try it for myself in January 2024 for only 62,500 miles + $32.70.

A one-way flight from London (LHR) to Abu Dhabi (AUH) flying in Etihad’s First Class Apartment would have cost almost $5,000; therefore, I scored an 8 cents per point redemption when utilizing AA miles for this awesome flight.

Katie Seemann, News Editor & Senior Content Contributor

My best redemption of 2023 isn’t necessarily the one with the best cents-per-point value. It’s the one that opened my eyes to the awesome value of premium economy.

I flew on American Airlines Premium Economy from Munich International Airport (MUC) to London Heathrow (LHR) to Philadelphia International Airport (PHL) to John Glenn Columbus International Airport (CMH) this summer for just 40,000 American Airlines miles.

American Airlines Boeing 787 Premium Economy 9a and 9c
Image Credit: Katie Seemann

I had intended to book business class flights for this Europe trip, but it was peak travel season, and I had almost zero flexibility in my travel dates, so availability was basically nonexistent. That led me to book a premium economy ticket for my daytime flight back to the U.S.

I found that premium economy was a fantastic option, especially for this 7.5-hour daytime flight from Europe. I didn’t need a lie-flat seat to sleep, and the extra space and upgraded amenities in the premium economy cabin were enough to make the flight very comfortable from start to finish.

Plus, premium economy award tickets are much easier to come by than business class tickets, especially if you’re flying with more than 1 person.

That experience made me feel comfortable booking a premium economy flight on KLM from Amsterdam to Chicago next year. I paid just 24,000 Citi ThankYou Points, which were transferred to Flying Blue for that flight — an incredible deal and one that I may not have jumped on if I hadn’t had such a good experience with the premium economy this year.

Keri Stooksbury, Editor-in-Chief

Points are only valuable when you actually spend them, and my husband and I have had a few thousand Marriott Bonvoy points hanging in our accounts for years.

As our family is a little larger (2 adults and 3 kids), we consistently found occupancy issues across Marriott hotels when trying to book an award room that could accommodate our entire family.

This spring, I was super pleased that we combined and liquidated our lingering Marriott Bonvoy balances at the chic Johannesburg Marriott Hotel Melrose Arch, where we stayed overnight at the beginning and end of a safari vacation.

Johannesburg Marriott Hotel Melrose Arch queen beds with twin bed
Johannesburg Marriott Hotel Melrose Arch. Image Credit: Keri Stooksbury

The awards cost 13,500 points per night, and given the nightly cash rate at the time, we got around 1.2 cents per point in value based on UP’s valuation. Most importantly, we finally used these points we had been hanging on to for way too long.

My other favorite redemptions this year have been on World of Hyatt Guest of Honor stays at Category 1 and 2 Hyatt hotels across India (Hyatt Regency Delhi and Hyatt Regency Jaipur Mansarovar) and the UAE (Andaz Capital Gate, Abu Dhabi).

Andaz Capital Gate Abu Dhabi loungers umbrellas
Andaz Capital Gate, Abu Dhabi. Image Credit: Keri Stooksbury

These low-point awards of 5,000 to 8,000 points have delivered suite upgrades, club access, and free breakfast, all thanks to a little help from my Globalist friends.

Lori Zaino, Content Contributor

My best redemptions each year are always transferring Chase or Amex points to Iberia Avios

In 2023, I was able to transfer points with a 30% bonus and use Iberia’s sweet spot to fly between Chicago (ORD) and Madrid (MAD) in business class on the A330 for 34,000 Avios each way, off-peak — one of the most affordable ways to get a lie-flat seat over the Atlantic.

Because it’s tough to find award availability on more than 2 business class seats for any given Iberia transatlantic flight, I’ll use 17,000 points each way to fly my family of 3 between the 2 cities in economy, off-peak in 2024.

Iberia flexible view
Image Credit: Iberia

While not nearly as glamorous or comfortable as business class, it’s an easy and affordable way to get my husband and son from our home in Spain to visit family back in the United States.

Final Thoughts

From Hawaii to Abu Dhabi and beyond, our team did not let distance stand in their way when it came to redeeming their points and miles. Whether it was a bucket-list trip they checked off or just a way to make a trip happen without spending hard-earned cash, the Upgraded Points team put on a masterclass of redemptions in 2023. The only challenge is figuring out how to top it in 2024.

Spoiler alert: we already have a few ideas!

The information regarding the Hilton Honors American Express Aspire Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

Chris Hassan's image

About Chris Hassan

Chris holds a B.S. in Hospitality and Tourism Management and managed social media for all Marriott properties in South America, making him a perfect fit for UP and its social media channels. He has a passion for making content catered toward family travelers.


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