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How I Searched For & Booked A “Free” Ticket to Cuba Using Miles from 2 International Loyalty Programs

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airline miles cuba award travel
Photo by Balint Földesi.

How I Booked My Flight to Cuba Using Miles

Last week I wrote about a crazy mileage run to Panama City I had put on hold as part of my quest to get Executive Platinum thanks to the AA Elite Fast Track. I actually ended up letting that itinerary go, only to put a similar one on hold and just before I bit, a crazy idea came to mind.

I was reading an article about how the U.S. further loosened restrictions on travel to Cuba, which just reinforced my belief that I have to get their soon before the masses take over. (I legally qualify under one of the 12 allowed reason to travel to Cuba, so it will be completely legal.) Then I remembered that I was going to be in Panama. What a perfect sidetrip!

Booking Cuba with Miles

Since none of the U.S. programs allow you to book travel to Cuba at all, I looked towards international programs for help. I had previously read that Avianca Lifemiles lets you search and book Cuba travel online, so I started there. I actually had 20K Lifemiles just sitting in my account with no planned use, so it was a perfect fit!

My first search on the Lifemiles website was from PTY-HAV using their “Smart Search” functionality. This is what I saw:

airline miles cuba award travel

So according to the website there aren’t any coach awards available, but I could get business class for 15K in each direction. Since I only had 20K Lifemiles in my account, I would have to purchase 10K more for $170.30. (Not a bad price, but not one I need to pay given I have plenty of points in other currencies.)

Here were the available flights:

airline miles cuba award travel

As you can tell by now, the “Smart Search” function only searches Avianca and TACA flights. Since those airlines don’t fly directly from PTY-HAV, I needed to perform the search another way. Back to the homepage. This time I forced it to search Copa. They are also a member of the Star Alliance and they fly directly from their hub in Panama City to Havana.

airline miles cuba award travel

Eventually I learned that the Lifemiles website was showing me screwy information when I searched the roundtrip. (Only business class flights were available.) When I searched the flights as one-ways, I was able to see coach availability on the return. The Lifemiles website is very frustrating to use, so be prepared before you go in.

I also found at times it would show a day had no economy availability, but when I clicked around I could find flights. It was strange and not the most useful, but it did work fine enough in the end. Ultimately I settled in on two flights that worked with my schedule. Business from PTY-HAV and Economy from HAV-PTY.

airline miles cuba award travel
This is not my exact flight, but I am using this to display the cost.

Avianca charges 20K miles one-way in business class from PTY-HAV on Copa. Since that one flight wiped out my balance, I needed to find another currency for the economy return flight. Most airlines charges 15K-20K on this route, so I turned to an airline where I already had a chunk of miles, Singapore.

Singapore charges 35K roundtrip in economy on this route or 17,500 miles each-way. I already had a chunk of about 60K miles sitting in my account for a Suites award I was going to book, but wasn’t able to. Singapore is also a transfer partner of almost everyone, meaning I can easily replace these miles whenever I need to.

Booking All 3 Flights

airline miles cuba award travel
My cheapest cash option to Cuba.

Before booking the flight to Panama on American or the Business class flight to Havana on Copa with Lifemiles, I called up Singapore and verified the space on the flight I had seen on the Lifemiles website. (Everything matched up perfectly.) The agent quickly booked the ticket for me and at the same time I booked both other tickets online.

Here is what my flight to Cuba cost:

  • Copa flight from Panama City to Havana in Business Class – 20,000 Lifemiles + $66 USD
  • Copa flight from Havana to Panama City in Coach – 17,500 Singapore Krisflyer miles + $26

Cheapest direct economy ticket on that route, $559.70.  So I spent 20,000 Lifemiles + 17,500 Krisflyer miles to save $467.70. (Although I am also flying in Business Class one-way.) Not the best redemption value overall, but these were miles basically just sitting there, so I am happy to have the cash in my pocket.

My Schedule

The way things worked out with the flights, I will be landing in Panama City in the morning and flying out to Cuba late that same night. This will allow me time to book some sort of a tour out to the canal for the day. I think that works out great.

I will then arrive late in Cuba and have two full days to explore Havana before flying back to Panama on the morning of the 3rd day. I will then have another full day in Panama where I plan to explore the old city and see some more of the sites. Then I fly back home via MIA and JFK! It is going to be crazy!


It is amazing how a timely elite fast track promotion can get the wheels rolling on a cool trip. I had always known I would get to Cuba at some point soon, but never had thought about how the pieces would fit together. Yes, I only have 2 days in Havana, but that is better than no days. Either way it will be another adventure made significantly cheaper by miles & points!

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Shawn Coomer
Shawn Coomer
Shawn Coomer earns and burns millions of miles/points per year circling the globe with his family. An expert at accumulating travel rewards, he founded Miles to Memories to help others achieve their travel goals for pennies on the dollar. Shawn also runs a million dollar reselling business, knows Vegas better than most and loves to spend his time at the 12 Disney parks across the world.

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    • Hi Linda. I have taken the trip. In Panama I stayed at the Hyatt Place which is in a very good location downtown. I have also heard good things about the Crowne Plaza near the airport if you need to stay in that area. In Panama I stayed in a homestay or casa particular. I used this site to find it.

  1. How come you dont have a booking service bro! Cmon man! Set up your own call center! I would call you!

    Also, do you have a trip report on the Bermuda Triangle and what you did inside the vortex of the 6th dimension? Just wondering…

  2. Great idea. I was looking out of other Caribbean nations and having trouble. It makes sense with Copa as a SA partner out of pty.


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