Get Started

Learn more about Credit Cards, Travel Programs, Deals, and more.

Why I Almost Smashed My Computer Booking My Last Trip

This post may contain affiliate links - Advertiser Disclosure. As an Amazon Associate, we earn from qualifying purchases.

Frustrations That Happen While Booking Award Travel

The Frustrations That Happen While Booking Award Travel

I recently planned what I thought would be a simple trip.  It turned out to be anything but easy when it was all said and done. I will go through the steps with you and hopefully you can find some joy in my misery.  Sometimes we love making the least complicated things difficult.  Knowledge isn’t always power it seems!

Trip Details

The plan was simple, a quick weekend trip to St. John’s Newfoundland. Myself and a buddy were going to fly up early on a Friday morning and come back Sunday.  We would probably only get a day and a half on the ground but it is a location I had been wanting to check out for a while.

St. John’s looks a whole lot like Ireland.  It has the cliffs, the ocean, picturesque lighthouses, and hiking trails. It even has the Irish pubs that of course have live music and serve fish and chips to go along with it.  A friend told me it is the most Irish place not in Ireland. I really enjoyed my time in Ireland so I thought this was worth checking out.

Air Canada had a flight leaving from Detroit that connects in Toronto, easy peasy.  Total flight time came in right around 6 hours including the layover.  Air Canada is a Star Alliance partner so I told my buddy to book it on United for a mere 25,000 miles and $65 in taxes and fees.  This was a $700 cash ticket so excellent value, especially in economy.

I of course did not follow this simple booking, at least not at first, and that is when things went off the rails.

Frustrations That Happen While Booking Award Travel
I hope to see similar views in St. John’s

Why I Had To Complicate Things

I could have easily booked the trip with United miles but I wanted to save my Ultimate Rewards points.  Even though I profess always using miles, I like to use my UR points last. My reasoning is two fold. The first reason is that they are harder to earn because the 5/24 rule and the lack of welcome offers I am able to get.  The second reason is that they have a true cash value of 1 cent a piece so I think of them as an emergency savings account too.  If I were ever in a big bind or had a huge unexpected bill come my way I could easily turn them into cash.  That adds a level of security should something tragic happen.

So now you know why I didn’t go the easy route and book the flight with United.  I decided to use the Star Alliance program to my advantage and focused on Citi ThankYou points.  I had just padded my stash with 60,000 points from the Citi ThankYou Premier card.  ThankYou points are the least valuable currency in my opinion so I look to use them first when I can.

This left me with a few options, mainly LifeMiles and KrisFlyer miles. If you are ever wondering which miles you can use for your flights just go to AwardHacker and select the flights and specify which points you want to use.  It is one of my favorite travel booking tools.

I had decided to go with LifeMiles because the transfer times were quicker and my buddy had already booked his flight.  I didn’t want the award space to disappear while waiting on a transfer.  That is when the trouble started.

Transferring to LifeMiles

So I went to LifeMiles to get my frequent flyer number so that I could transfer my ThankYou points in.  I usually save my logins so that it is easy to get in and out of accounts. The problem was my LM account didn’t save.  I searched my email for my frequent flyer number but the first email they sent when I set up the account had a disappearing number.  I guess once you click through the link the number goes away.

Frustrations That Happen While Booking Award Travel
Notice something important missing in that sentence?

No problem, I will just go through the find my account steps on their website.  Pretty much any place lets you do this fairly easily.  Not LifeMiles though you need your FF number to be able to perform the find account option.  Great!

So I called LifeMiles to get my number and after a 10 or so minute hold I spoke with an English speaking representative.  I gave him all of my info and went through the hoops and then he asked me for my pin.  I attempted it 2 times but I don’t think I ever went through the steps to ever fully set up the account. That means I never actually set up a pin.  LifeMiles policy is to not give you your number without your pin.  For some reason they can’t email it to the account on file or confirm your identity some other way.  He said I would need to email a whole list of things to their customer service department, like a copy of my passport, address, pictures of my first born child etc. (that last part was a joke).  Suffice to say it was way to much “proof” in my opinion and I didn’t have the time to wait on a response.

That is when Citi’s ThankYou program came into play.

Transferring Citi ThankYou Points

The work around to not having an account was to set up my wife with a LifeMiles account and transfer ThankYou points to her account to book the flight.  Easy enough and it would be quicker than waiting on customer service to email me my frequent flyer upon confirming my DNA results.

Setting up her LifeMiles account was not without issues because well it is LifeMiles.  I kept getting errors the entire time and every login username I tried came back as used.  This was an error since I got to the point of trying dasglpo3093lk234 and still nothing!  Finally after pounding my keyboard over and over again it accepted a username.

So I then went back to Citi to perform the transfer to LifeMiles.  I attempted the transfer 3 different times and got an error each time.  I was boiling over at this point and called Citi to have them do it for me.  Once I got on the phone the automated system told me she had 0 points in the account.  I hung up and checked my wife’s LifeMiles account and there sat 25,000 miles.  Somehow they made it through the constant errors.

via GIPHY  (What I Wanted To Do)

Booking the Flight

After all that I finally had the miles where they needed to go and I could get this flight booked.  I plugged in all of the necessary info, selected my flights and then hit enter.  Wouldn’t you know it another effin error screen!?!?!?! I tried it several times and every time I selected my flights I would get an error.

Errors and LifeMiles go hand in hand but errors usually occur when submitting payment.  I picked up the phone and called LifeMiles again.  They asked me where I lived and upon telling them they said there is a malfunction on the site and to try again later.  I tried later and the next day but had no luck.

Funny enough if I selected a United flight in the US etc. the booking would go through with no issue but Air Canada and LifeMiles were not on speaking terms it seems.  Now at this point you can email their customer service with all the booking info, along with the name of your unborn child or something stupid like that, and they will book it for you.  I simply didn’t have the time to wait on this.  I had lost my patience and I didn’t want the award space to vanish.

Once again I picked up my lifeline to the LifeMiles customer service department to attempt to book a flight for myself using my wife’s account.  I am sure they were going to tell me she needed to call them.  I would have rather walked through fire then attempt that discussion!  So after 30 minutes on hold I hung up, chucked my phone across the room, and booked the damn flight with United miles.


What can we learn from this, outside of the fact that LifeMiles has a sole sucking, time eating, horrid system?  That sometimes simplicity is best even if it costs a little more.

Now I am stuck with 25,000 miles in a program I despise that has a terrible 12 month expiration policy.  I will have to try to use them on an airline I hate, United, or maybe take a trip on Lufthansa just because etc.  I will find a way to use them I am sure but I hate having something I don’t really want and I will stress about using the miles until they are gone.  Looking at you too Wyndham!

Just in case you were wondering I tried to plead with Citi to reverse the transfer since the partner’s system was not working properly.  I got a “pound sand” response.  The kicker is that I had to actually call back in to get their response since they never called me back to tell me.  This is right before her annual fee is due…I bet you can guess where that decision is leaning! Also I checked the award space a day after I booked and one of the flights were gone so I don’t regret the decision to go ahead with United.  I probably took the last spot but better safe than sorry.

Has anyone had a similar experience booking a trip?  Share your misery below…make me feel better!


Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

New Card - Capital One Venture X Business 150K!

Capital One Venture X Business earns 2X miles on everyday purchases plus up to 10X in bonus categories. You also get access to Capital One lounges plus an annual travel credit & anniversary bonus. Right now you earn bonus_miles_full.

Learn more about this card and its features!

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Mark Ostermann
Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Using Lifemiles is a challenge and frustrating. As someone who has had the relative ease of using American Airlines AAdvantage miles for several transoceanic flights over the last eight years, today’s experience with Lifemiles was a mess. I found a business class LAX-WAW on LOT for a suitable date in June using the Aeroplan website, but in several attempts to find the flight on, I decided to call them to see if they could book it for me. Their phone menu is not exactly clear, and I waited on silent hold for some 15 minutes. The agent denied that the flight was available for Lifemiles. Relogging in to Aeroplan, I still found the flight available, and with one seat available, but when I logged in to yet one more time, chosing StarAlliance from the airline dropdown menu, the flight was not there. Logging once more, I ended up with the Spanish language interface but decided to go with it since I know a little Spanish. This time I decided to be creative and from the dropdown menu I decided to chose “LOT” from among all the SA airlines, bypassing “StarAlliance”. Yes! The flight was there so I knew I had to grab it right away.

    What a grossly non-intuitive user interface has. The hints at found on some websites were somewhat of a help, but not completely. And phone customer service was a joke — it seems like most of the agents were determined not to be helpful.

    Despite an email confirmation of the flight, I checked the LOT website within a few minutes of booking on Yes, it was there!

    As a frustrated new user of Lifemiles, I am happy to have nearly exhausted the points from my account with this transaction.

    • When things go smoothly LifeMiles are great but when there is an issue it is a whole production for sure. Glad you were able to get it booked though.

      • My summer travels plans, like those of so many others, have been decimated by the coronavirus, and in mid-March I realized I couldn’t go at all. LOT has cancelled most flights through the end of May, but not (so far) in to June. LifeMiles has so far not been as generous as other reward programs, and I fear but fully expect that I’ll lose the waiting game to see if LOT cancels my June WAW flight — otherwise, it appears that I’ll have to pay $200 to LifeMiles to cancel the June booking I mad in December with any hope that I can get my points restored. And even then, there’s no cheap way to extend the validity of those points past December 31, last I checked. Or maybe they’ll allow me to rebook within a year of December 2019 ticketing. I’m sure Poland is delightful in the winter months for those who don’t mind the bitter cold, the constant gray skies, the rain and snow, and 3 p.m. sunsets. I prefer the summer, but it looks like I’ll be locked out of a summer 2021 rebooking without paying substantial $$$ to LifeMiles.

          • I got my LifeMiles points originally by converting Citi Thank You points. I hadn’t thought of doing that again to extend the life of my LifeMiles, so if that’s what you mean, I’ll give that a try. Thank you!

          • Yeah transferring in a few more should extend them another 12 months. My pleasure JR

        • As the summer of 2020 and the pandemic wore on, I called LifeMiles to see if I could cancel the flight and get my points reinstated, due to the pandemic. Yes, they cancelled my booking and reinstated my points, all without fee. Further, LifeMiles automatically extended the life of my points too, again due to the pandemic.

          Another more recent LifeMiles nightmare: now that I am planning my long delayed trip to Europe for summer 2022, using those old LifeMiles, I was able to find a suitable ZRH-YVR-SJC booking on AirCanada last fall for September 2022. It all went well: I got ticketed by LifeMiles on AC within a day and chose my seats on the AC website right away. Then idly browsing my flight on the AC website a couple of weeks ago, I found that 1) my booking had been changed to terminate in SFO instead of SJC, and 2) my seat selection had vanished, and I could no longer manage my booking on the AC website. I called AC, waiting on hold for an hour, to find out that, yes, AC had changed the second leg from SJC to SFO some weeks earlier. I was ok with that, but the AC agent said that LifeMiles had to reissue the ticket, but hadn’t done so. So, on to another adventure with LifeMiles telephone customer service to ask them to reticket this involuntary change in my booking. I went through the usual circus that evening of trying to reach someone at LifeMiles. For those who haven’t had the “pleasure”, there are multiple and confusing options to press on your phone keypad when calling in: chose the wrong one and you’ll end up in LifeMiles purgatory in which the agent, if one answers within 20 or 30 minutes, can’t or won’t help you. On top of that, the audio quality is so bad that it’s hard to understand the agent, and hard for the agent to understand you, not to speak of the accents involved. Even my attempt at speaking Spanish to one very nice, sweet agent went nowhere as the line quality was as bad as my Spanish. After a couple of hours, I was finally able to reach an English-speaking agent, and with barely usable line transmission quality, who seemed to understand the issue. It easily took him a full hour to research how to get LifeMiles to reissue the ticket, get approvals, confirm with me that AC’s new routing was not done at my request, send me an email with LifeMiles’ take on the new routing, my confirming it with him that it was correct and acceptable. Only then could he get the LifeMiles ticketing wizards to actually reissue the ticket, and at no charge to me since the rerouting was involuntary. The actual confirmation that a new ticket was issued came the next day by email from LifeMiles, at which point AC was happy to deal with my seating.

          As long as your booking with LifeMiles is not complicated and doesn’t involve LifeMiles telephone agents, they offer some great rates on intercontinental flights, and without fuel surcharges. Hurray! Throw in complications of your own or the carrier’s, you better hope you find plenty of patience in yourself , long waits, clear phone signals, and agents who know what they’re doing (and have the power to do it).

  2. I just spent a week going thru all the airlines/mileage programs, having one after the other fail me. ExpertFlyer didn’t help. It showed a lot more availability than I could find, and flights that didn’t exist. Finally, a 50k Virgin award popped up (Delta wanted 420k!) I could jump on with TY points. Then an AA award helped get one of us home. So after all the hair pulling and stomach churning, I ended up with 2 Bus class JFK-AMS, and 2 First class ATH-JFK for 185k points+$2800. Couldn’t get it totally free but I’m relieved it’s done! BTW, AA agent said NO long term layovers allowed in US gateway when I wanted the award to be ATH-JFK-SFO, staying in NYC for 5days. Has the policy changed? Or should I have hung up and called again?

    • Sounds horrible Amy but I am glad you finally got something to work out. Did you end up getting hit with the BA taxes and fees when using your AA miles?

      • 85K miles + $361. Could have been worse. But for First class, I’ll happily pay it.

        Did I miss an opportunity here:
        “AA agent said NO long term layovers allowed in US gateway when I wanted the award to be ATH-JFK-SFO, staying in NYC for 5days. Has the policy changed? Or should I have hung up and called again?”

        • Edit: dig some more digging and it looks like AA doesn’t allow stopovers on awards from what I have read.

  3. United domestic intra-zone is where it’s at, Mark.

    Only 7,500 miles each way. But as you know, I’m kinda captive to stupid UA at our regional airport.

    Make lemonade. And then smash your computer.

    • I have been a looking. Their coverage out of DTW is pretty horrid. I will figure something out eventually I am sure…then their system will freeze…and then I will smash my computer for sure lol.

  4. I’ve never tried LifeMiles but I sure have had trouble with Citibank. I collected ThankYou points for a while but found it so frustrating trying to book travel through their portal that once I used up the points I cancelled the card. Every single time I tried to use their booking engine it failed in one way or another and I ended up having to do the booking over the phone. I’m done with TY points. I know what you mean about hesitating to use up UR points. The Chase travel portal is so powerful and easy to use that it makes their points more valuable and then you don’t want to use them. Because… they are so easy to use. There’s something wrong with that logic, but I’ve been sucked in by it too. I’m glad you finally got your booking – sounds like a fun little trip!

    • Citi has it’s challenges for sure! Thanks I am looking forward to it. Hopefully it lives up to my expectations.

    • I don’t know that there ever is really a good time to buy Delta Skymiles. They usually cost more than they are worth. You are better off transferring Membership Rewards points to Delta etc.

        • That price isn’t bad at 1/2 cent a piece but I wouldn’t purchase them unless you had a known use for them. Would work well for an upcoming 5th night free stay etc.

  5. I have Krisflyer miles from a Singapore Airline trip to Hong Kong which is enough for a one-way flight I wanted to use on Alaska Airlines from SFO-SEA. Problem is, with Singapore Airlines, you cannot book award flight using their website or there is no way I know of. I called the Singapore Airlines 800 number and the Krisflyer phone number and was on hold each time for 50 minutes until I gave up the first times. SA customer service finally answered and said I had to deal with KF customer service. KF finally answered and I could not understand what he was saying since he had such a heavy accent and finally he said he would have someone call me back. The next day, I received a call from a SA customer service rep from Singapore which was very nice but could not find any flights available from SFO-SEA on any Star Alliance partner using award miles. In the end, I used my UR reward and AS miles to book the flights for my family. So, my question is, who know how to us Krisflyer miles from Singapore Airlines to book a flight the next time around? I even sent an email to SA customer service and there has never been a response! Very disappointed.

    • Wow sounds like they let you down. Alaska is not a Star Alliance partner, so I’m wondering if the agent was looking in the wrong spot for space. This partnership is still newish so maybe they just didn’t know.

      I have received good service in the past by calling their Singapore based CS with Skype or another cheap service.

      To sum it up. AS awards can’t be booked online and maybe you need to make clear it isn’t an alliance partner. Also try calling Singapore itself since they tend to speak good English and are generally more knowledgeable. It does seem they dropped the ball here though.

  6. Mark – i just made my first Lifemiles booking last month. saved tens of thousands of miles (Asiana flight – they priced it out far below their own published prices, which were cheap to begin with). it worked but when i called to book it, i was told that I had to wait for THEM to call me back to finish the booking…which happened 4 days later. Too stressful for me. Never again.

    • The program has a lot of value it is sad that their system and culture don’t allow it to be better. I have heard of people having to wait to be called back to pay for the taxes on their flights…which is insane that only a few specific people can do it.


Please enter your comment!
Please enter your name here