Behind The Booking – My Family’s Recent South American Adventure

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Our trip started in Medellin for the Flower Festival. This parade marks the end of the festival and signifies when farmers used to carry the flowers from the small villages into Medellin on their back.
Our trip started in Medellin for the Flower Festival. This parade marks the end of the festival and signifies when farmers used to carry the flowers from the small villages into Medellin on their back.

Colombia & Chile In Two Weeks

Over the past couple of weeks, my family and I spent some time in both Colombia and Chile. Do to various scheduling issues, I was not able to book our flights until the last minute and we faced other issues with my wife having to leave early and my son and I ending in different places. In this post I’ll break down the bookings and show how a family can travel for cheap, even at the last minute.

Getting To Colombia

As I mentioned before, certain scheduling prevented me from booking this trip far ahead of time. For flights down to Colombia, luckily American Airlines has great availability through Miami. I found availability for our dates to Medellin, Bogota & Cali. (The example below is of upcoming dates.)

An example of award space between MIA & MDE for 3 people in the month of September.
An example of award space between MIA & MDE for 3 people in the month of September.

After some research, I found out that Medellin was having their Flower Festival on the weekend of our visit, so we decided to start our trip there. Since we left in early August, peak season pricing was in effect and each one-way ticket cost 17,500 Aadvantage miles.

The total cost for 3 people was 52,500 miles plus $61.80 in taxes. (I am a AAdvantage Platinum so the close-in booking fee didn’t apply. Otherwise it would have been an additional $75 per ticket.) The cheapest one-way fare on this route was about $426 on Spirit, with the next cheapest being around $700. 17,500 points plus $20 per person was a great value.

The next cheapest one-way on a normal airline was about $700.

Medellin To Bogota

Our next stop after Medellin was Bogota. To get there, I had hoped to use British Airways Avios to fly on LAN Colombia between the cities. When I booked the trip, flights between the two cities weren’t available with miles for the dates that we needed. I had hoped that last minute availability would open up, but it didn’t. Our backup plan was to hope that one of the local carriers such as Viva Colombia would have cheap fares or as a very last resort, we would take the overnight bus.

Shawn Reece eating amazing meat on a stick in Medellin, Colombia!
Shawn Reece eating amazing meat on a stick in Medellin, Colombia!

Normally various carriers sell one-way tickets between MDE-BOG for around $50. Since this was the big weekend of the festival, these prices went up to about $100. With no award space opening up, we finally decided to take the nine hour bus ride which cost about $30 per person. In the end we saved on a hotel night and saved quite a lot of cash, but it wasn’t the most comfortable experience in the world.

Leaving Colombia

My wife was only able to stay for the first week, so she ended up flying home while my son and I continued on to Chile. Her return ticket was 17,500 miles plus $94 in taxes on American Airlines.($38 of the taxes were returned at the airport, so the net cost was $56.) In total then our cost for her travel roundtrip from Las Vegas was: 35,000 Aadvantage miles & $77 including all taxes and excluding the bus fare.

LAS-MDE & BOG-LAS for $815.
LAS-MDE & BOG-LAS for $815.

The cheapest air ticket for this route was once again Spirit. If we factor in bag fees then her cost would have been $865. In comparison American was $984 and LAN was $966 for the same route. (LAS-MDE & BOG-LAS). In essence we exchanged 35,000 miles for a savings of $788. ($865-$77 taxes.) This means that we redeemed our Aadvantage miles for a value of 2.2 CPP. Not great, but not bad and considering we have a ton of them thanks to Citi, it made a lot of sense.

A comparison of flight costs for (LAS-MDE & BOG-LAS).
A comparison of flight costs for (LAS-MDE & BOG-LAS).

As I mentioned before, my son and I went on to Chile. Once again I was hoping to use British Airway Avios to fly on LAN between Bogota & Santiago, but no availability ever came open. Luckily I had some Avianca Lifemiles and was able to patch together a booking for two tickets in coach between the two cities.

While Avianca didn’t have Saver availability on the BOG-SCL flight, since I was using their miles I could still book. Their cost for the one-way coach ticket was 17,000 miles each or 34,000 total. I only had 23,000 miles in my account, but luckily Avianca allows members to buy additional miles at 1.5 cents each. Our two one-way tickets from Bogota to Santiago ended up costing 23,000 Lifemiles plus $257 including all taxes. The cheapest cash option for that single one-way flight for our dates was $1105 on LAN, so I thought it was worth it.

Street artist in Bogota. We bought two of his masterpieces for $10!
Street artist in Bogota. We bought two of his masterpieces for $10!

A lot of people prefer to use Lifemiles for so called “trick” fares, but in this case I felt it was a good redemption. Had I planned ahead and found availability on LAN, then I probably would have used 12,500 Avios instead for coach or even 25,000 for business class. Unfortunately that wasn’t an option for our dates, so I pulled out my bag of tricks and made it happen.

Leaving Chile

Booking our tickets out of Chile was a bit tricky since I was heading to Washington DC to speak at the Family Travel For Real Life Conference and my son was flying home. He is 14 years old and thus can travel without an adult, but I wanted for us to be on the same flight to the United States.

Thankfully our departure date from Chile fell during the first few days of American’s offpeak season for redemptions to Southern South America. During the offpeak season a one-way award ticket in coach between Santiago & the United States is only 20,000 miles plus $53 in taxes. That is an amazing deal and one I fear will go away when their new award chart comes out next year after the merger is completed.

My son's itinerary for his flight home.
My son’s itinerary for his flight home.

Fortunately I was able to get two tickets on the American Airlines flight from Santiago to Dallas with my son connecting home to Las Vegas and me on to Dulles. It was a perfect redemption for our situation since he didn’t have to fly internationally by himself.

Our Flight Costs

While it would make me feel really good to add up all of the one-way flight costs to come to a total, that isn’t realistic since I could book these routes as one ticket. In the end my son and I each redeemed 37,500 Aadvantage miles, 11,500 Avianca Lifemiles and spent $202.10 in taxes & fees including the cost of the additional Lifemiles.


As you can see above, my cheapest paid option for the flights would have been $1765 including the flight from MDE-BOG. Since that was running about $100, I will subtract that out to say I could have paid $1665 for the flights I took. Subtracting out taxes, I spent 49,000 miles total to save $1462.90. This means that I redeemed my miles at about a rate of 3 cents per point. (It gets complicated if I take out the cost of the additional Lifemiles purchased and doesn’t effect the overall calculation very much.)


For my son’s trip back to Vegas the redemption value is even higher. While he redeemed the same number of miles, the cost for him to make all of the flights was $2033. This means that we redeemed 49,000 miles to save $1830.90 and redeemed at a value of 3.7 cents per point. A great redemption in my opinion!

What Does This Mean

Booking trips for multiple people can be difficult. When you are doing it at the last minute things can get even harder. In this case I was able to use my knowledge and flexibility to get us the trip that we wanted on the dates that we wanted for a very small amount of money out of pocket.

Hiking down Santa Lucia Hill in Santiago, Chile.
Hiking down Santa Lucia Hill in Santiago, Chile.

While many people love to fly up front, I would rather travel in the back than not travel at all. Unfortunately there wasn’t business class availability on any of these routes for the dates that we were flying or we probably would have opted to fly up front. Being flexible is the key, especially when you are booking at the last minute.

Final Tallies For Flights Only

Jasmine: 37,500 miles, $77 in taxes. (Retail: $865).

Shawn (Me): 49,000 miles, $202.10 taxes & fees. (Retail: $1665).

Shawn Reece: 49,000 miles, $202.10 taxes & fees. (Retail: $2033).

GRAND TOTAL SPENT: 135,500 miles + $481.20. Retail Value: $4,563!

I also want to note that I will be redeeming Barclay Arrival points to cover most of the actual out of pocket costs. I also use certain cash back strategies to ensure that my net out of pocket cost in the end is less than $0!


While this post is a little long and complicated to follow, it shows that last minute family travel is possible, even when schedules are complicated. We all started in the same place, but ended up taking different routes back on different days to meet our schedules. My son and I were even able to fly on the same flight back to the U.S. before splitting up to go to our final destinations.

This type of redemption is a great reminder of why this hobby is so amazing. Of course I never would have spent $4,563 on a last minute trip to South America, but I didn’t have to. On a final note, some of the AA miles did have a small cost of accumulation, but I offset those with cash back which I mentioned above.

If you have any questions please let me know!

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  1. Congrats on only writing “Columbia” once. Can’t figure out why Americans have so much trouble with that one. I guess it’s the way we say it.

    • Thanks for catching that. I wrote Colombia eight times in the article and somehow messed it up only on my first go.(Shouldn’t have messed it up at all!)

      I believe Columbia is the proper spelling of the river right? Most people probably mess it up since spell checkers probably see it is a valid name.

      Anyway thanks again and I have fixed my one misspelling in the post!

  2. Shawn – great blog. Just discovered it thanks to Points with a Crew. Could you share the routing for the outbound?

    I think AA miles to SA can be a great value but am increasingly finding lots of crappy routings to get to the hub from which you fly internationally. It’s very hard to get to DFW or ORD or JFK non-stop.

    • Thanks! I can definitely share the routing!

      The routing for the three of us getting there was LAS-MIA-MDE.(LAS-MIA was a redeye with a two hour layover in MIA arriving in MDE at around noon. Overall not bad. Coming home from Colombia my wife flew BOG-MIA-LAS with an hour layover in MIA. Coming home from Chile my son flew SCL-DFW-LAS (60 minute layover in DFW) and I flew SCL-DFW-IAD with a 2 hours layover in DFW.

      • That’s a great routing. Being ORD-based, unless I can find a non-stop from ORD (and AA has cut back significantly on long haul flights from ORD – only have daily to LHR now, CDG/FCO/NRT/PVG/PEK/HEL/DUB/DUS are all seasonal or less than daily), I end up needing to do ORD – xxx – DFW/MIA – South America. xxx is often TUL, CVG, LIT, CID, etc. Very frustrating!

        • I have noticed it is very difficult to get hub to hub direct flights on AA. Often times it is hard for me to get flights to/from Las Vegas as well. I have resorted to going in and out of LAX if need be, however it did work out great on this trip.


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