Challenge! 40K to Far Away


About a month ago, I hosted an annual Frequent Miler business meeting.  The idea was to take a step back from the day to day blog writing in order to look at the big picture.  We know that our priority is to make our website great.  What does great look like?  What steps do we need to take to get there?  A big part of our vision is to be not only informative, but entertaining too.  Towards that end, we remembered that I used to create crazy points-related challenges.  For example, I once challenged myself to do New York City for $19 per day (results here).  Later, I challenged myself to earn a million points & miles in one month (due to alliteration concerns, that million mile madness month had to be in March or May — I chose March).  You can view all of the old blog posts on the subject (in reverse chronological order) by clicking here.  Finally, in  2015, I challenged myself to earn 1.2 million Virgin Atlantic miles in order to visit Necker Island.  While it only took me 7 months to earn the miles (read about that here), the actual trip didn’t occur until October 2016.  You can read my summary of that trip here.

Now, we’ve gone years without a significant new challenge… until now.

40K to Far Away

This fall, Nick Reyes, Stephen Pepper, and I will meetup in a convenient city to kick off our new challenge.  Our goal?  Get as far away as possible.  Our budget?  40,000 points and $400.

Each of us has been assigned a transferable points currency.  We are allowed to use up to 40,000 points, as follows:

  • Greg the Frequent Miler (AKA me): 40,000 Chase Ultimate Rewards points
  • Nick Reyes: 40,000 Citi ThankYou points
  • Stephen Pepper: 40,000 Amex Membership Rewards points


We expect this to be fun!  And, equally importantly, it should be a great opportunity to highlight sweetspot awards available through each of the transferable points currencies: Chase Ultimate Rewards, Citi ThankYou Rewards, and Amex Membership Rewards.

Why 40K?

The idea for this challenge originated with the idea that most credit card welcome bonuses these days are for 40K points or more.  The question was: how far could one go with a single bonus?  Then the question of taxes and fees and other incidentals came up.  How much should we be allowed to spend?  Ultimately we decided to base the answer on the total standard signup bonus for the Chase Ink Business Preferred card: 80K Ultimate Rewards Points.  With 80K Ultimate Rewards points, one could cash out 40K points for $400 in order to take care of taxes, fees, airport transfers, etc.  And 40K points would remain for booking awards.

The Rules

The goal is to use the budget (40K points + $400) to get as far away as possible.  How do we measure success?  We don’t know.  We debated whether we should measure distance from origin to destination, but that didn’t seem right.  After all, someone could potentially fly all the way around the world and end up 0 miles from the start.  How about measuring the combined distance of each individual leg?  Maybe, but should we really count it as going far away if Stephen rides a merry-go-round 35,000 miles?  Ultimately we decided that we’ll know success when we see it.  And, if we don’t, it will still be fun debating it!

That approach goes for most of the rules we discussed.  We’d rather go light on rules and have fun debating who won and who cheated later on.

But we do need some rules, so here they are:

  • Beginning with the first mode of transportation, we must account for all costs within the 40K + $400 budget.  This means that we need to track payments for food, airport transfers (not counting the original transfer to get to the starting location), lodging, visas, etc.
  • This is a one-way challenge.  We do not need to return to the starting location.  When Nick declares success standing with a flag at the North Pole, he can then return home however he wants.
  • We cannot accept transit/lodging/food help from readers.  In other words, we can accept help in terms of advice (e.g. hey Stephen, you can book this flight for only XYZ miles!), but we can’t accept a ride to the airport, lodging, whatever.

Nick Reyes

Nick is the most experienced award booker in our group.  He volunteered for Citi ThankYou points.   He has all kinds of ideas for how he’ll use those points, but hasn’t yet shared his ideas with the rest of us.  I suspect that he’s planning to use one of the sweetspot award charts found in the Etihad program (here’s an example), or maybe he has finally cracked the Lifemiles code.  The great thing for him about using Lifemiles is that Avianca does not add fuel surcharges to awards.  So, he won’t have to use much of his $400 cash budget to book long flights.

Stephen Pepper

Stephen is, by far, the least experienced award booker in our group.  He chose Amex Membership Rewards.  This surprised me a bit since Chase points are arguably easier to use.  I don’t know what tricks he has in mind.  He might be planning to take advantage of the current 30% transfer bonus to Virgin Atlantic.  If he went all in with this, his 40,000 Membership Rewards points would become 52,000 Virgin Atlantic miles.  He can then use our US-Centric Virgin Atlantic award chart to find the longest distance flights that he can afford.  For example, he could fly economy all the way to India for only 20,000 Virgin Atlantic points:

The problem with the above suggestion is that it would use up most of his $400 cash allowance since Virgin charges around $290 in fees for that booking.  It still might be worth it because he would only need to transfer 16K of his Membership Rewards points to get enough Virgin Atlantic miles for this booking.  With the remaining 24,000 points, he may be able to get pretty far.  Of course he would only have $110 left to pay for fuel surcharges, airport transfers, food, and lodging, so I actually hope he has a better plan than this (unless he thinks that arriving in India would be a win?)

My strategy

With Chase Ultimate Rewards, I feel like I have a huge advantage in this game.  In addition to being able to transfer points to a number of airline programs, I can also use points for 1.5 cents each towards travel via the Ultimate Rewards portal (thanks to my Sapphire Reserve card).  So, for example, I could straight up buy $1,000 worth of airfare and call it a day.  Why $1,000?  My 40,000 points are worth $600 in travel.  And I could throw in up to $400 cash.  But, I have a better plan (I think).

1. United award positioning flight

Chase points transfer to United 1 to 1.  I want to use United miles to get from our starting city to another airport.  If I’m extremely lucky, I’ll find a flight for as little as 5,000 miles one-way (United has begun charging that little on select flights at select times).  More likely it will cost 10K or 12.5K (depending upon the length of the flight).  This positioning flight is important to set up the next two steps of my diabolical plan:

2. $400-ish flight to very far away

I’ll be scouring the web for the cheapest flights to the farthest reaches of earth.  If I can find a flight for $420, for example, it should cost me only 28,000 Ultimate Rewards points to purchase that flight through Chase’s travel portal.  Importantly, Chase will let me choose how much to pay with points and how much to pay with cash.  Depending upon how many points I spend in steps 1 (above) and 4 (below), I’ll need to adjust accordingly.  The cash portion will come out of my $400 cash budget.  If I’m really, really lucky, I’ll be able to book a super cheap Delta flight to somewhere far, far away.  This would be great because as a Delta Diamond Elite, I have access to global upgrade certificates.  I could use one of these certificates to hopefully fly up front.

3. Free United Excursionist Perk

Nick wrote at length about United’s Excursionist Perk in the past.  More recently, Travel is Free published an awesome discovery regarding this feature.  Specifically, it should be possible for me to book a round trip award consisting of a cheap outbound leg (step 1, above) and a cheap throw-away return leg (such as Chicago to Newark).  In the middle of these two flights, I should be able to book a completely free excursionist award flight as long as it starts and ends in a single zone (United’s zone definitions can be found here).  This means that I should be able to fly the length of South Asia, or North Asia, or Europe, or even Oceana.  Which zone I choose will depend on where I end up in step 2 above.

4. United award return leg

If by some miracle, I have enough points left over to fly all the way back to the US from wherever I end up at the end of the Excursionist perk, then great.  More likely I’ll book the cheapest throw-away segment I can find.  It simply has to end in the same region as the trip started.  I’m hoping that I can find a 5K award flight to mark the end of my trip.  Most likely I would never fly this segment.  This is here simply to make the free Excursionist Perk flight possible.

My maybe totals

Here’s how the above might shake out:

  1. Positioning flight: 10K points transferred to United + $5.60
  2. Cheap long distance flight: 25,000 points + $200
  3. Excursionist Perk flight: Free
  4. Return leg: 5K points transferred to United + $5.60

Totals: 40K points, $211.20.  If it shakes out as shown, I would have nearly $190 budget remaining for food, lodging, whatever.

When and Where

We will announce the starting date and location of this challenge once each of us has booked at least the first leg of our journey.  The primary reason for keeping this secret at first is because we don’t want too much help from readers.  For example, someone who knows a killer award deal might spoon feed the exact solution to one of us.  If that happened, it wouldn’t really be fair… or fun.

Your turn

Are you excited about this challenge?  Do you have advice for me, Nick, or Stephen?  Please comment below!

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