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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For the next idea – how about “Around the World in 80 Ks”

Find/book/travel the best or most interesting RTW trip with 80K points in the currency of your choice (Chase/AmEx/Citi or individual airlines).

Glenn Lee

I would absolutely replicate this challenge to see how I stack up against the gurus!

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Sincere question – what are you all going to tell your grandkids?

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[…] consist of me crying about being stuck with ThankYou points and how I can’t possibly win the #40Kfaraway challenge, I’m sorry to disappoint. This post is about a great option or two I’ve already […]


Good luck fellahs. It sounds like an awesome challenge. I wish I could join you…but some of us have old-fashioned work

[…] can also read Greg’s announcement about 40K To Far Away here. That has more information about the challenge, along with the limited rules we’ve come up […]


While I would never encourage someone to pass up elite benefits even in a game I would not be as willing to declare them the winner when those benefits created an advantage that others coming to the starting gate did not have……….obviously each of you has an idea where you are going to go so I am interested in seeing how it plays out………and I can’t imagine any of you charging off into the world without an idea how you are going to get home……well maybe Greg……….


Also, it’d be pretty epic to fly somewhere interesting and do a car rental adventure. Using status like Hertz 5-star or National Executive Elite, you might be able to ride in style to some really far-flung places that a flight alone wouldn’t be able to take you. Fly into Beijing and take a BMW convertible across the Gobi dessert? Or to Tanzania and take a Land Rover across an old trade route? Food could be cheap (road stall stands, soylent shakes, lol) and depending on where you go and what car you get, you might be able to camp out in or right next to it (to save on accommodations).


you guys are so creative!

Boris Minevich

You guys excluded AA mikes by default as nothing transfers into AA. No tricks there but you can get far with a straight AA partner chart.


I don’t think either 3 of you would violate the spirit of the challenge, Greg, but if one of you was to win an Arby’s Free Flight/Hotel to Hawaii (& use your points/miles for the rest), for instance, is that legit? A rule is no freebies from readers but what about other sources besides the usual?


Nick, if you have the Citi Rewards+ CC that gives you 10% of your TYPs back, does that mean you could redeem 40K TYPs and get another 4K TYPs to redeem? Cheating or fair game?

Nick Reyes

Sounds totally fair to me :).


Game on then!

Nick Reyes

Only, I don’t have the Rewards+ :_(

Stephen Pepper

As much as I’d like to say cheating, that’s totally fair game.


Spot on. These types of posts were always great. Glad to see you’re bringing them back.


Definitely looking forward to seeing the outcomes!

Before I read the whole post, my initial assumption was a round-trip booking for 40K + $400 allowance for taxes/fees/positioning. To me that seems more relevant to using a credit card bonus than only taking half a trip. But, regardless, this is definitely an interesting experiment with lots of opportunities as well as seeing where your different personalities lead you based on interests.

I *already* learned something when you noted the Virgin chart to India and I peeked at the premium economy listings I never looked at before. Decent comfort for a fair price IMO! So, count this as a successful challenge even before it officially begins.

Dr. McFrugal

This sounds like a fun and fantastic challenge / game! Can’t wait to see what everybody comes up with. I imagine the destinations will be to some places where the cost of living and touring are very low so to take your money even further.


So I know readers aren’t supposed to help out, but can you stay with friends and family to buffer costs?

Nick Reyes

Now now — you and Drew can’t go buying up Airbnbs around the world to help Greg have an even cushier path!


I’d prefer to see who can get the most lavish, luxurious trip for 40k and $400, not the furthest away. F and J for 40k.


Love the idea! It sounds so much fun already. Here are some silly thoughts.
1) Can we get to vote who had the “Best” trip? Farthest is non-subjective in my opinion – which is just miles traveled.
2) I think it should be required to show how you would get back (you don’t have to book it, but should show screens that how you can return and what amount of points/miles/cash are needed for your return trip).
3) I think eating local food is required (can’t just bring a bunch of top ramen and call it a meal). Local food doesn’t have to be expensive local food. What’s local should be defined…you guys can decide on how to define it (i.e. Google search? Trip Advisors’, etc…)

I am so looking forward to this! Thanks, you guys!


Dang, Greg, this is old school miler stuff!!!!! LOVE, LOVE, LOVE IT. Hope you guys will also do a a bit of trip reporting during this as well.


It’s a fun contest idea. I know where I’d go. Are there any time limits? Like, do you have to stay at destination one night or one week? Or how long do you have to get there? 40,000 miles is still enough to take you just about anywhere that you can reach with regular airlines if you don’t mind economy class. After that, it’s a question of how far you can get with ground transportation. A lot of it comes down to trading comfort vs. cost.

Nick Reyes

And food! Don’t forget that food and lodging come out of the budget as well.

Thank goodness I like peanut butter sandwiches.



Any though of allowing readers to participate? It would be fun if some readers would also do it and post what they pulled off.


Just wish I was retired as I’d be all over this……


or double the budget and each of you takes a reader along as a guest


Doesn’t make a whole lot of sense, and is a lot less interesting, if you don’t include the return journey. Planting a flag at the North Pole isn’t really a “win” if it you’ve simply deferred the bulk of the cost for the return. Increase the budget if you must, but include the return. This will also allow you to judge success not just based on how “far” away you each get, but also on how much time you each spend away and how much interesting activity you each accomplish.

Nick Reyes

Thanks for the feedback!

First of all, I don’t know why Greg assumes the North Pole. Clearly, the South Pole would be farther. But I like that he’s underestimating me from the jump.

As to return journey, my thoughts on that are two-fold: first, the return should be possible for the same amount of points (or fewer depending on whether any of us gets creative in adding additional destinations). So simply figure double the budget or less to get back (though I like your suggestion and think that in the end, each of us should plan a theoretical journey as to how we’d get back for the fewest points / cash).

Second, I thought a return journey for 40K would lead to a lot less variance in what we do. The purpose (in my mind) was to (hopefully) show three entirely different journeys / strategies with three different currencies. If we demand a there-and-back out of it, the likelihood of us all looking to the same award chart increases and therefore I suspect would lead to at least a slightly less interesting outcome. At least, I think. Maybe we’ll try that in a future challenge.

As to judging success, how much time and how many interesting activities will likely be part of the debate. I look forward to seeing who gets the farthest away, who gets the “best” trip, etc. I further look forward to you explaining to Greg and Stephen why you think I won.


Great idea! will be fun to follow. Another fun challenge would be who can fly around the world within ~3 days using the least number of miles as possible (using avg redemption rate to equalize currencies)


Nick & TYPs both love the far-flung, a match made in Timbuktu?!

Matthew Harlan

Excellent idea. The first post I ever read from you was on your Necker Island challenge and I’m pretty sure I stumbled onto it as a link from another source who found it interesting.

T. Jones

I’m excited by this challenge and look forward to reading more. This is the sort of thing I find really helpful as a
regular reader.. Nick’s choice of ThankYou points has me curious to see what he’s planning. I love my Membership Rewards points, but Stephen’s going to have to stay mindful of the transfer costs. Small amount can add up! It blows my mind that Greg chose last and wound up with Ultimate Rewards. Seems too easy. He better watch out for the other two!

Nick Reyes

I’m excited, too!

Quick note on transfer costs: You only pay to transfer Membership Rewards to US airline programs. There is no fee to transfer to programs like Virgin Atlantic, ANA, Etihad, British Airways, Singapore, etc. You just pay when you transfer to Delta, JetBlue, or Hawaiian….and I doubt Stephen will be using any of those three programs (though I hope he does use up some of his budget on that! Ha!).

T. Jones

I guess I’m showing just how new to all this I really am. Lol. Good to know that! I learn so much here!


Sounds great challenge and I look forward to seeing where each of you end up.

However, I’m not sure that I agree with you using Global Upgrade Certificates. If average Joe was to replicate this challenge using bonus points from signing up for the cardm, s/he may be able to get to the same location but certainly not in the same comfort. I think you should be traveling within the means of 40,000 points and $400.


Credit card benefits I agree with… because anyone who has the card would receive those benefits. But elite benefits no.

It may also impact on where you decide to travel to. If you are considering two destinations there is no doubt if one route would allow you elite benefits then you would be swayed by that instead of just seeing how far you can travel and where to.

However, it’s your challenge so you set the rules! 🙂

Nick Reyes

I’ll chime in since it was my idea to allow elite benefits. My thought was that just like you’re suggesting, a normal human who has elite status often makes choices based on that elite status, for better or for worse. Most people who play this game have one elite status or another. I thought using the benefits that you’ve already earned seems like fair game and realistic. and furthermore potentially gives Greg a leg to stand on as to why he bothers to manufacture Delta elite status; so he can win competitions like this

it also makes it more fun because even if Greg gets farther, everyone can complain that he cheated.


Look forward to seeing how it pans out, but would be interesting to see another version where no elite status benefits can be applied 😉


It is a trap, Greg. Nick put you in a no-win situation. ^_^

Stephen Pepper

If Greg earned status through flying due to a corporate job, that might be a little unfair. However, he largely earns it through manufactured spend which, in theory, is an option for anyone. I’m therefore happy to sit jealously in economy while he’s at the front of the plane on the challenge.


I wonder if most people who play this game do have elite status with airlines…You would know better than I, but I would have my doubts. Hotel status, certainly, as those come with credit cards. My initial response was the same as Euan’s.

Nick Reyes

That’s an interesting question. Anecdotally, from meeting readers at conferences, it sure feels like many people get into miles & points because they have a job where travel is required and they would like to be able to leverage some return from that business travel to be able to enjoy a nice family vacation or two to balance out all the time they spend away from home. Indeed, I feel like most of the first blogs in this space were aimed at business travelers as those were the folks spending enough times on planes and checking in to hotels to be curious about how many points they could earn, what status, what the credit card could get them, etc (e.g. see the movie Up in the Air with George Clooney).

Is it “most” readers today to whom that applies? I definitely don’t know. But neither would I be surprised at all to hear it if 1 out of 3 readers held some sort of airline elite status. Coincidentally, 1 out of 3 of us (Greg) does. And he didn’t even earn it from business travel — he did it a way we all could. Seems legit and relevant to a segment of readership. Obviously that won’t apply to all readers — but nothing would apply to everyone and I think it’ll be interesting to see whether Greg’s status leads him to make questionable decisions (loyalty programs are after all designed to make us do irrational things). I think it’s further interesting for a Delta flyer if Greg leverages Chase Ultimate Rewards to further his chase for elite status and/or maximize his benefits since many regular Delta business flyers might assume they should be focusing on Membership Rewards or an all-SkyMiles strategy.

By the way, I have an offer for a fast track to AA Gold courtesy of my Hyatt Explorist status. If it works out that it would come in handy on the trip, I wouldn’t hesitate to start the match challenge and take advantage of the benefits. I think the three of us share an eye for maximizing the system to do as well as possible. I don’t know for sure that whatever we book will reflect that, but I think if Greg ends up being able to do this thing up front, that demonstrates just how cool this game is when you get invested in it.

I’m pretty excited to see how this all shakes out. In think I changed my plan twice today so far :-).


Thanks for the detailed reply! Exciting post and idea. Looking forward to following!


This is a great idea! I do agree with Euan that you shouldn’t use elite benefits since you can’t assume most of your readers have those benefits. You can assume all of them have credit cards that provide perks. In any event, looking forward to it!


Love this!

Jorge R

At last something interesting to read! It’s been forever since I’ve been excited about a post from the miles and points bloggers.


This sounds like a ton of fun to read, follow and participate in- have fun!


I wish I could be part of this game!

Steve S

This is awesome


Sounds like fun. Can’t wait to see the results.