Guest Post: 10 Lessons Learned While (trying to) Redeem 1,000,000 Points & Miles

Robert Dwyer is a deal hound who spends hours each day thinking about points, and how to use them for awesome family vacations. He writes about wine at The Wellesley Wine Press. You can follow Robert on Twitter: @RobertDwyer

Earning a view like this might take a bit more work than you initially think!

Earning a view like this might take a bit more work than you initially think!

Related Reading: Lessons Learned While Earning 1,000,000+ Points & Miles

Compared to signing up for credit cards for lucrative signup bonuses and manufacturing spend to meet initial spending and/or spending threshold bonuses, I find redeeming airline miles for award flights much more difficult and frustrating.

The specific parts of award redemptions I’ve been frustrated with is searching for/finding space available on the routes and dates I want to travel – especially when redeeming for a family of four. But even when searching for just one passenger it can still be hard to find availability at saver levels, even with a fair amount of date flexibility, and even when searching very far in advance (as well as very close in).

A typical scenario goes something like this… You know you want to go to some specific destination with points & miles. Say it’s Hawaii, or Europe, or Asia – whatever. You know you want to go some time during summer vacation. So you start searching 330 days out right when availability opens up. And you search 6 weeks before the flights. You search all year and no flights ever come up at saver levels. To me, if an airline says a flight to Europe should cost 60k miles in economy and I’m willing to stockpile 240k miles for my family to travel, and I have a reasonable amount of date flexibility, I think I should be able to get the award at some point. Maybe not the perfect dates, and maybe not the perfect route, but there should be a reasonable award available at some point. But this often isn’t the case, and I think this scenario is the one that single handedly causes people to say “forget it – points &F miles are a sham”.

And it’s a good thing every single person on the planet isn’t playing the points & miles game. It would only make competition for award space more fierce. But what drives me bonkers is when I’m stalking a flight with reasonable date flexibility around a school holiday and award availability never comes up. Or when I do find availability the flight times change beneath me and changing the flights becomes difficult.

For example, I was looking to fly to Arizona around spring break which for us is the week after Easter this year. After racking up 150,000 Membership Rewards points last year for signing up for the AmEx Platinum and Gold cards I had enough points for 4 roundtrip flights from Boston to Phoenix in First Class. By transferring 160,000 Membership Reward points to Singapore Airlines around 10 months ago I was able to find connecting flights on United (through Houston) if I was willing to leave the Wednesdaybefore Easter. Cancellation fees were reasonable, we weren’t in the mood for international travel, we wanted to go to Phoenix to visit family especially since it’s been a while, and since there wasn’t any saver level award space in economy I booked 4 tickets in First.

But then 6 months before the flight, United changed flight times beneath us. Instead of a 2 hour layover we now had a 7 hour layover. Brutal! So I called to see if I could change to a different flight. They couldn’t find anything so try back later. I called every couple months and searched online repeatedly and nothing popped up.

But then I noticed some new flights pop up on United’s website. I was in luck I thought! But when I called Singapore to book the flights they said they couldn’t book them because it was a mixed cabin booking (one leg in Economy, one leg in First). I said that didn’t bother me but they still wouldn’t allow me to book it.

So a few weeks later availability showed up all in First – no mixed cabin. I was in luck I thought! But when I called Singapore they said they can’t book the flights because it was on US Airways and US Airways was leaving Star Alliance before the flights would occur. I said “they haven’t left yet – I should still be able to book it”. They wouldn’t budge.

So I asked if they could just cancel our return journey with the long layover because I found some reasonable paid fares for that part of it. They said they could only cancel the entire ticket and United might not release the outbound award space once they cancelled it.

So 2 months before the trip I said “forget it – this just isn’t going to work out”. And I started to re-think travel plans for the year. By then I’d racked up points & miles in a bunch of different programs, including United and Chase Ultimate Rewards. Since Chase Ultimate Rewards points can be instantly transferred to United I had quite a stockpile of United miles.

I’d been saving United miles for a potential Summer 2015 trip to Germany for European Delivery of a BMW (the idea that got me chasing after points & miles in the first place). I wanted to get a sense of what award availability looked like from BOS – MUC in summer months for *next* year so I’d been keeping an eye on award space to Europe on Lufthansa *this* year. Although United devalued their award chart while I was “on the treadmill” racking up points & miles, and business class awards on partner airlines went from 100k to 140k round-trip I still felt it was a good use of points. Even if Lufthansa doesn’t offer the greatest business class in the world (now we’re getting greedy).

Let's all hope for the NEW Lufthansa Business Class!

Let’s all hope for the NEW Lufthansa Business Class!

When I looked for award space on the direct Lufthansa flight from BOS-MUC 330 days in advance I saw very little award availabilty. I kept monitoring it to see how it trended as the dates got closer and although economy award space still hasn’t opened up I suddenly saw wide open availability to Europe at saver levels the entire months of July and August: All summer! It seems like United’s increased redemption requirements for partner flights in premium cabins caused demand to plummet perhaps?

So I stepped back and thought: What do we really want to do? Italy. Italy would be amazing.

Sure enough award space was available on great dates at good times to Rome and/or Naples. I knew I could figure out lodging later so I set out to book the flights. Using United’s “above average but still often annoying” website I could see the availability. But I heard about this trick called a “free one way” whereby I could add a one-way flight in the US (for example) months before or after my main flight without adding any additional miles. Further sweetening the deal, there was good availability to Phoenix around Christmas which is probably an even better time to visit than Easter.

So I tried to book the flights as a multi-city flight online. Although each individual segment showed award availability, when I tried to book the flight online it wouldn’t let me. It just kept spitting out this ambiguous message that things didn’t work out and to call if I needed help.

I called and talked to a customer service rep and pieced together the flight. Indeed, saver level awards were available on all my flights.

But to get approval for the “free” one way she had to get approval for the routing. She did so I said I’d like to book it but would like the $25 per person fee waived since I can’t book it online. She said she couldn’t do that, and that I should be able to book it online – try again. I tried again – same error.

So I called back to ask whether I could also book one of the tickets using my wife’s United points and while I had the new rep on the phone he checked for the availability, found it was a valid routing, and said he’d waive the fee!

I started transferring points from my Chase Ultimate Rewards account and from hers to top off our United accounts with enough points (560k!). It took about 5 minutes for all the transfers to go through. They’re not quite instant but close enough for what you need in a situation like this.

But then when he went to process the award he found there actually wasn’t availability on one of the flights from Boston to Frankfurt. Doh! I was so close! My dreams of grandeur were dissolving before my eyes. A victim of phantom availability I wondered?

He poked around a little more and found an equally good connection through Munich. The taxes are actually a little less through Munich so it was a win win. 560,000 United miles and Chase Ultimate Rewards drained for $32,000 worth of travel. Wow.

This to me is an example of both the frustration associated with award travel and the potential leverage. On one hand this was an incredibly high involvement affair. Both the racking up of miles and the finagling around for award availability. But I could never justify paying for premium cabin international flights for the family. Or First class domestically. Or heck – even paying for “premium economy” seating. If I was employing a cashback approach to credit cards (as opposed to a point & miles approach) there’s no way I could have justified paying for these flights.

And I probably couldn’t even justify paying for 4 economy class tickets to Europe in the summer at $1,500 a piece. $6k? That’s a lot of money. I couldn’t justify the trip in my mind even at that price. Points & miles help me, psychologically, justify the splurge in my mind. As a result even though they can be a pain in the neck they can also be very fun to play with – especially when it works out well.

So how are we getting back from Phoenix? There was tremendous award availability on direct flights from Phoenix back to Boston for 4 people in First Class on US Airways at saver levels. And since AA and US Airways merged I could now use my AA miles to book the flights for 100k one-way for 4 people in First. US Airways leaving Star Alliance was now working to my advantage!

I am absolutely thrilled and looking forward to these upcoming trips.


Here are 10 lessons I learned while redeeming points & miles the last couple years…


1. Keep a diverse portfolio of points & miles

Although it’s not good to have your eggs in too many baskets, having a lot of options at your disposal when it comes time to search award availability is a great thing. Especially flexible points like Chase Ultimate Rewards, AmEx Membership Rewards, and AmEx SPG which can be transferred to airlines and hotels for high leverage award redemptions.

2. You never know what’s going to happen

If I looked back at the trips we’ve taken and planned in the past couple years, many of them weren’t on my radar screen a couple years ago. While it’s good to have a specific goal you’re working towards in mind when racking up points & miles it’s okay to be a little aimless.

Go with the flow and be enjoy life!

3. Have a flexible list of desirable vacations you want to take in the next 2 years

This serves three purposes:

  1. It keeps you dreaming about awesome vacations which in itself is fun
  2. Enables you to have a stack of desirable vacations you can swap around depending on award availability
  3. Helps you stay focused on doing what you really want to do

Life is too short to be restricted by geography and money. Dream big about what you want to do and make it happen.

4. Even if you’re not sure how you’re going to use it right away, it often makes sense to jump on limited time massive signup bonuses

After signing up for the AmEx Plat and Gold cards I had 160k Membership Rewards points. I was frustrated to discover how hard it was to transfer those points to a Star Alliance partner for award travel on Lufthansa without incurring expensive fuel surcharges. I thought I may have focused in the wrong program for a while.

But after racking up a bunch of United points & miles and Chase Ultimate Rewards points I saw that with enough time, patience, and finagling I could have enough points & miles that did enable both the trip I wanted to Europe and I’ve still got enough Membership Rewards points for 4 domestic round-trips in First Class on United. Or who knows what else might come along.

5. Connect the dots

Increasing, what I’m noticing in this points & miles game is that the most value is derived by connecting various techniques you learn. It’s not just “fly on United for all your paid travel, get United card to fly family in Economy class on United once every two years”. That’s a sucker move. That’s low leverage. Read FlyerTalk, read blogs, learn about this stuff. It does change over time but establishing a better fundamental understanding of how credit card signup bonuses, manufactured spend and award travel works can be a significant source of highly discounted travel.

6. Find situations where you can book a fallback flight with low/no change fees as a placeholder

We flew down to fly down to Florida for February break this year. This is an extremely competitive time to travel. Flights, especially ones at reasonable times and routings, seriously cost like $800 round-trip if you want to leave on Saturday and return on Saturday.

I was able to find the outbound flight on US Airways in First Class for 68k Lufthansa miles. This might be a questionable use of Lufthansa miles but given the situation worked out very comfortably. On the return flight I didn’t see award availability on US Airways but I found reasonable one-way fares using Southwest points coming back on Thursday.

I booked those then decided to come back on Wednesday. Southwest is great because they don’t charge change fees nor cancellation fees. So I actually got points deposited back into my account for changing to a cheaper day of travel! And if I wanted to take my chances on US Airways award space opening up I could. We ended up taking the direct flight back using Southwest points (on AirTran actually) and it was great too. I enjoyed the flexibility.

7. Rework the way you think about vacation to be more open to last minute vacations

Everyone is wired differently in terms of how far they like to plan ahead for something. If it were up to me I could book each vacation a couple months ahead of time depending on how I felt after my last couple trips. In this game, it seem to me that you’re best off if you either plan way ahead (like 330 days when most carrier bookings open) or you don’t plan much at all.

Finding last minute travel deals sounds great, but they rarely seem to come up during school vacations. Especially for air travel. But I think it does pay to be able to jump on an award redemption opportunity that pops up just a couple weeks before departure. In fact some award travel (like Lufthansa First Class booked via United for example) doesn’t even open up until 2 week before departure.

It can be tricky planning contingencies operating this way. For example, meeting up with other family members or juggling school break childcare coverage if you do/don’t end up going away. But I’m going to work on taking more trips this way depending on how we’re feeling closer in to travel dates.

8. Try booking sample itineraries to get a sense for award availability trends important to you

I’m always poking around on and booking sample itineraries. And heck, I even got lucky booking reward redemption at saver levels on Delta one time! But be looking far out and close in to get a feel for how viable certain itineraries are going to be. You might discover a great opportunity and even if you don’t you’ll develop more confidence knowing when to pounce on a good award.

9. Know which carriers have the best availability for the routes important to you

Generally speaking, revenue-based award redemption programs like Southwest, JetBlue, and VirginAmerica have good availability but this is only because the number of points it costs for an award seat are a function of how much the seat costs. So while there’s good award availability there’s little opportunity for high leverage redemptions.

Of the legacy carriers, United has slightly above average availability, American is somewhere in the middle, and US Airways and Delta are below average. We’ll see what happens when American/US Airways start working as one. Hint: Mediocre availability plus poor availability definitely won’t equal above average availability.

Delta is going to a revenue-weighted points earning scheme where the more you pay for a flight the more points you earn. Although they still have a zone-based award chart, and they say they’ll have better saver availability in the future, they’re still on most loyalty traveler naughty lists. They need to give away a lot more miles via credit card signup bonuses to make their program worth exploring in my opinion. If you live in a Delta hub it’s got to be a rough situation.

10. Realize that award charts represent a best case scenario that might never be available

I’ve fallen into the trap of feeling like points & miles are a scam because those doling out the points can change the rules at any time. And indeed, as the economy has improved and the airlines aren’t hurting, the last couple years have been brutal. But there are still some massive redemption values out there.

It helps me if I look at award charts as a best-case scenario rather than something I’m entitled to if I earn enough points. I then work this into the mix, along with relative award availability trends of each airline, when considering how much each mile or point is worth to me.

I’m reminded of this quote from Jerry Maguire:

“Hey, I don’t have all the answers. In life, to be honest, I’ve failed as much as I’ve succeeded. But I love my wife. I love my life. And I wish you, my kind of successes.”

― Dicky Fox, written by Cameron Crowe


Questions? Feel free to ping me on Twitter: @RobertDwyer

Further Reading: Lessons Learned While Earning 1,000,000+ Points & Miles

Question of the Day: What tips and tricks would you share with someone frustrated with redeeming points & miles?


  1. My own thoughts: These are the exact same circumstances that almost every person goes through when starting in the points game. Earning the points is a completely separate task than redeeming them, with the latter being much more difficult as explained above. This is why award booking services exist, and why people willingly pay for it!

  2. I can totally relate what was said here! We are a family of five and everywhere we go it is an army! I plan my trips more than a year out as our schedules are limited by school and work, which means we often travel during peak summer times or Christmas/New year holidays. Gathering the points takes even longer than a year. Our last trip was 3 weeks in China over this past holiday, lots of planning going into it, but I did manage to fly everyone in Cathay first class from SFO! 😉 the kids giggle all the way to HK! oh hiring award booking service takes away the fun, I would much prefer do it myself!

    • That’s awesome you’ve been able to make it work for your family. I’m inspired and totally agree that when it works out it’s all worth it. Cheers!

  3. Robert,
    This is a great piece! I like your “connect the dots” especially and would add one of my own: “just get over the pond”. Both Europe and Asia have tons of short hop opportunities using cash or MR/UR/Thank you on budget airlines (esp. Europe when you add in trains) and if I find 4 tickets that get me anywhere in Europe and match my dates I don’t ask questions…I just book!

  4. Great article! I had a lot of expiring miles but couldn’t use them… I discovered lately a website ( that allows to trade miles from one program to another even for other loyalty programs, It helps a lot!

Speak Your Mind

Your email address will not be published. Required fields are marked *