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Redeeming Miles For Our next Adventure: Santiago, Chile

Last updated: January 12,2023
Originally Published: May 12,2020
by Jameson Lamie

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Our next international adventure with points is to Santiago, Chile!

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Santiago skyline, which includes the tallest building in Latin America

I just wrote about why I love United Airlines frequent flyer miles, and United miles helped us book one part of our roundtrip business class airfare.  So now an appropriate time to discuss how we use our travel credit cards to redeem miles and score an awesome weekend trip.

Yes… a weekend trip.  We’ll be taking a four-day Labor Day weekend for our quick trip to Santiago and back.  It sounds a little crazy, but since we both took so much time off from work already for our RTW trip, we can’t afford to take off many more days.  But that doesn’t mean we can’t still use our points to travel. 😉

Since it’s been 1.5 years since we booked our RTW airfare, we’ve had plenty of time to accrue credit card points and frequent flyer miles.  So a quick weekend trip is a perfect opportunity to spend those points/miles and also experience other airlines’ long-haul business class.

So why Chile?

Most importantly, there was award availability over Labor Day weekend.  I wanted to go where our points would take us, but I also wanted to make sure we were able to leave after work on Thursday in order to take full advantage of our four-day weekend.

Santiago has also been on our radar for quite some time.  We had a blast on our first trip to South America (Peru and Bolivia), and we immediately planned a return trip (thanks to points!) to Colombia and Ecuador.  We’ve been hoping for an Argentina/Uruguay/Chile trip since returning from Ecuador, but haven’t been able to make it happen.  But…

Going to Chile now will give us more time in Argentina and Uruguay during a future trip.  Air travel in South America can be expensive, especially between Chile and Argentina/Uruguay.  By going to Santiago separately, we’re able to give ourselves more flexibility and time for future travel to Southern South America.

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It’s not Patagonia, but Cajon del Maipo is a nice day trip into the Andes from Santiago.

Our Flights

Washington, DC to Santiago, Chile

Before I knew what I was really doing with credit card points, I randomly signed up for the American Airlines credit card.  I probably followed some link from The Points Guy, and I then quickly learned the points were harder to redeem than the website led on (imagine that 🙄).  In any case, I’ve had about 60,000 American Airlines miles collecting dust in my account for the past three years.

I tried using those 60k miles multiples times, but American Airlines’ award availability is lousy.  Washington National Airport is an American Airlines hub, and it seemed like the only award availability I could find was to Raleigh or Charlotte.  And that’s only the domestic leg of the itinerary.  The odds of actually finding award availability on a connecting flight and then the international flight on a day I actually wanted to flag was nearly impossible.

By some miracle, I found award availability over Labor Day weekend both from Washington Dulles airport to Miami and then Miami to Santiago.

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Our business class flight itinerary to Santiago.  The late departure on Thursday means we only needed to take one day off from work to make a four-day Labor Day Weekend.

The one-way business class fare cost 57,500 American Airlines miles, and the taxes only cost $5.60.  That definitely beats redeeming those points for some lame domestic ticket that would probably only cost $200 out of pocket.

However, that’s only one of the flights to Santiago.  I still needed a way to book another ticket for Taryn.  Luckily, Alaska Airlines is a partner with American Airlines.  Alaska Airlines also has an advantageous award chart.  Since there was already award space available on the flight to Santiago, I could use 57,500 Alaska Airlines miles to book the second award ticket from DC to Santiago.  I already had roughly 30,000 Alaska Airlines miles, and I quickly earned another 30,000 more miles by signing up for the Alaska Airlines credit card.   After the sign-up bonus, I had enough points to book the second ticket for Taryn.

American Airlines recently upgraded the business class seats on aircraft from Miami to Santiago (Boeing 777-200), so I look forward to comparing it with other premium class seats we flew during our around-the-world trip.  It’s a long overnight flight to Santiago, and hopefully, we can get a few hours of sleep in the lie-flat seats. 😀

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Lie-flat business class seats for our American Airlines flight to Santiago (photo courtesy of The Points Guy)
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A previous American Airlines business class meal.  (photo courtesy of The Points Guy)
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American Airlines business class seats for our flight from Washington Dulles airport to Miami. No need for anything too fancy on a short domestic flight.  (Photo courtesy of The Points Guy)

We have a pretty tight connection in Miami (1 hour, 8 minutes), so fingers crossed that we won’t have any delays out of DC.  That also means that we likely won’t have the opportunity to use the newly renovated American Airlines Admirals Club in Miami.  I’m sure they’ll make sure we’re well-fed during our two flights, so I’m not too worried.

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The American Airlines Admirals Club in Miami (Photo courtesy of The Points Guy)


  • Total airline miles:  115,000 (57,500 American Airlines miles and 57,500 Alaska Airlines miles)
  • Total taxes and surcharges:  $23.70
  • Cost of actual airfare: $12,544 ($6272 x2)
  • Monetary value of miles: 9.8 cents/mile that’s a fantastic valuation.  And it definitely beats the one-cent/mile you’d receive from something like the Capital One Venture card!

Santiago, Chile to Washington, DC

Once we booked our flights to Santiago, I knew it wouldn’t be an issue finding award availability on the flights home.  That’s because Copa Airlines (the national airline of Panama) consistently has wide-open award space, and as a Star Alliance member, can be easily booked with United Airlines miles.  

Copa Airlines takes advantage of the geography of its Panama City hub, which is a convenient midpoint between the U.S. and South America.  As a result, Copa Airlines doesn’t have any traditional long-haul flights, since the longest flight from Panama City is under 7 hours long.   The great business model for an airline… but that also means that Copa Airlines doesn’t offer any lie-flat seats on their aircraft.  So we’ll be flying in business class and treated special, but unfortunately, we’ll have to manage with these seats:

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Our Copa Airlines business class seats.  It’s not lie-flat, but also not too bad for quick back-to-back flights.

The one-way business class airfare costs 60,000 United Airlines miles plus modest taxes and fees ($47.86).  I had a few overseas trips for work last fall, so I had enough United miles already.  However, Taryn was about 30,000 miles short, so we transferred 30,000 more miles via our Chase Ultimate Rewards account.  Considering most of the expenses on our RTW trip was travel and dining, we earned a ton of credit card points  So no biggie transferring some of our points over.

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Our return itinerary from Santiago.  An early morning flight and short layover, but at least we’ll be back to DC in time for a Labor Day cookout.

The only thing that I’m not too excited about is a 3:21 am departure time from Santiago.  Definitely not ideal, and because Copa Airlines doesn’t have any true overnight flights, this is the closet thing to it.   We could have flown out of Santiago later in the morning, but the tradeoff is that we’ll be back at our house in DC with plenty of time for burgers on the grill for Labor Day.  We will have another short layover, so I doubt we’ll be able to hang out at the Copa Club lounge for business class passengers.

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Copa Club lounge at the Panama City Airport


  • Total airline miles:  120,000 United Airlines miles (or Chase Ultimate Rewards points)
  • Total taxes and surcharges:  $95.72
  • Cost of actual airfare: $2,664 ($1332 x2)
  • Monetary value of miles: 2.2 cents/mile

No, not nearly as good as the much better American Airlines business class fare with lie-flat seats, but still a decent valuation.

Overall, we’re paying $119.42 for international business class flights valued at $15,208.  It still blows my mind that these rewards credit cards were able to make our trip possible. If you want to learn how we do it, read more of our blogs or sign up to our travel concierge.

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