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This Just In... Check out the latest travel rewards credit card offers

My Travel Hacking Fail

By David Carlson / Last updated: June 20, 2015 / Credit Cards, Travel

We may receive compensation from companies mentioned within this post via affiliate links. Read our full advertiser disclosure. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
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My Travel Hacking FailOver the past year or so I’ve become a big fan of credit card hacking, or travel hacking as most people refer to it as.

I have been able to get hundreds of dollars in travel paid for.

Besides travel rewards, I’ve also received cash bonuses and other perks such as Amazon Prime.

But today I am not here to brag about any travel hacking successes. Today I want to talk about my travel hacking fail.

This was supposed to be a relatively quick and easy travel hack. What I learned is that travel hacking doesn’t always go as planned.

Read on to see my travel hacking fail and most importantly potentially avoid a similar fail!

My Travel Hacking Fail

There are lots of good things about the personal finance blogosphere. I’ve met some awesome people and received some great advice from other bloggers. It seems most people are afraid to admit their failures, though, especially when it comes to travel or “splurge” spending.

Since following legendary entrepreneur Gary Vaynerchuk I’ve learned to fully embrace failure. Failure is absolutely key to success. Not only that, but the faster you fail the better. I thought that was an important point to make before delving into my own personal failure.

This travel hack fail is extremely ironic because the hack was supposed to result in a free Vegas vacation. The irony is mainly due to the fact that I wrote a post about how (theoretically) you could go to Vegas for free through a variety of travel hacks. Let’s just say it didn’t pan out for us.

The trip costs that we were expecting to get for free were the flights and hotels. Let’s look at where each of these went wrong.

  • Flights

    There is a small regional airline called Sun Country that is based in Minneapolis. They are one of the more affordable airlines and one of the locations they regularly fly to is Las Vegas.

    Sun Country has one of the best credit card rewards out there. The annual fee is waived the first year and if you spend $500 you get 40,000 miles. There are no blackout dates though the number of miles you need varies depending on the date and destination of the flight. Needless to say this is one of the best airline deals out there.

    The first mistake I made was not plan far enough in advance. If my wife and I both opened Sun Country cards we were virtually guaranteed two free round-trip flights to Vegas. Instead I only opened one. It was still going to be a great deal as I should have had enough for one round-trip flight and one one-way flight.

    The problem is the miles required for the flight changed literally within a few days of me checking. The 40,000 or so miles i had on my Sun Country card would only cover one round-trip flight. I’d be shy of the one-way trip I was banking on by a few thousand miles.

    Cost of the round-trip flight? About $200. That’s $200 we could have had in our pockets if we had planned better.

  • Hotels

    The flight wasn’t the only thing we failed out. Arguably a bigger fail was our hotel strategy.

    As I wrote about in my post How to go to Vegas for Free and How to Get Up to 3 Free Las Vegas Hotel Rooms a Month, there is a game called myVEGAS Slots that is free to play and the points racked up can be redeemed for free hotel rooms, buffets, and more.

    Throughout the past year or so my wife and I have earned a ton of rewards points. You can redeem up to three per month. So between the two of us we would easily be able to get 5 free nights and only have to switch hotel rooms once (3 nights on one of our accounts and 2 nights on another). Every time I checked the rewards availability there was more than enough rooms available for this to be a reality.

    Just our luck, though, there was very few hotel room comps available for July. Some of them were only for restricted dates and there was essentially ZERO for weekend rooms (Friday and Saturday night). The only explanation I have for it is that they are much busier during the Summer months so they don’t need to give out free rooms to get people to come to Vegas.

    After checking and re-checking the rewards night after night we finally gave up and paid for five hotel rooms. Unfortunately for us our trip is Saturday through Thursday. Saturday night is more than double (or at times even triple or quadruple) the cost of a hotel on Monday through Thursday night. Add in the resort fees and we were out about $450.

So there you have it. Instead of paying only a few hundred dollars on resort fees, food and drinks, transportation, and gambling, we will also be paying approximately $650 for the flight and hotels that we thought would be free.

Lessons Learned from My Travel Hacking Fail

I learned a number of things through my travel hacking fail. They include:

  • Have more miles than you think you need – The cost of flights can fluctuate based on supply and demand. Make sure you have more miles than you think you need in case the cost changes. The last thing you want to do is miscalculate and end up paying hundreds (or in some cases, thousands) more than you thought you would have to.
  • Plan your trip far in advance – If we had planned our trip further in advance we could have at least avoided having to pay anything for flights. We would have been able to adjust our strategy and open a second Sun Country card. After all, we only needed to spend $500 for the flight. Instead we were out $200.

    This could have bigger implications if we were flying somewhere more expensive, like Europe or Asia, where miscalculating could literally cost you $1,000+.

  • Realize reward programs can change – Rewards programs can change. Virtually all travel rewards programs have disclaimers saying they are subject to change.

    When I browsed the myVEGAS slots rewards in the past there was always enough to cover 5 nights in Vegas, for free. Unfortunately the program changes and it wasn’t the case anymore when it was time for us to book our trips. Basically the way I view rewards going forward is that nothing is a sure thing until it’s booked and confirmed.

All things considered I’m glad that I failed at travel hacking on this trip. Even with only getting one free round-trip flight Vegas is still a really affordable trip for two people. There aren’t many places you can fly two people to and stay for five nights for free for under $1,000. Beyond that I also made the mistake of having the vacation start on Saturday instead of Sunday. Sunday nights are the expensive nights in Vegas; Sunday through Thursday the hotels are dirt cheap.

Another reason I’m content with the travel hacking fail is that we would really like to travel hack a vacation to Europe next Summer. For us to be able to afford this trip it’s extremely important that we get the flights 100% free.

We started working on this travel hack January of this year and we won’t be going on the trip until the Summer of next year. This will give us a ton of time to churn multiple cards and review (and re-review) our trip plans. We also consulted with a travel hacking “pro” and I will likely reach out to him a few more times to make sure that there are no surprises or changes that we need to be aware of.

Have you tried travel hacking? What challenges have you run into? How much time do you dedicate towards trying to reduce the cost of travel?
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David Carlson

David Carlson is the founder of Young Adult Money. He is a nationally recognized speaker and the author of Student Loan Solution (2019) and Hustle Away Debt (2016). His opinions have been featured on such media outlets as The New York Times, The Washington Post, Cheddar, NBC's KARE11, and more.
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Reader Interactions

Comments

  1. Jason@Islands of Investing says

    I’m definitely no travel hacker, and the credit card reward programs are pretty average here in Australia, but fortunately my wife is fairly savvy at planning our trips and getting the best deals. The thing I find scariest about these reward programs is that they could change in an instant, as you mentioned. A company goes bankrupt or just decides to do something different, and a whole load of careful planning can just go out the window!

    Love the attitude though of learning from your mistakes and sharing them for the benefit of others!

  2. Holly at ClubThrifty says

    Doh! Sorry D.C. That sucks. It sounds like you just need to start planning earlier next time. I usually find that booking flights and hotels 6-9 months out makes the difference in availability. I have even booked out as far as a year before.

  3. Andrew LivingRichCheaply says

    I’m no expert in travel hacking…I have a friend who has a spreadsheet to coordinate his cards as well as his wife’s cards.  He also has a spreadsheet to tell his wife which credit card to use at what types of stores to optimize the points.  I’ve run into some of the problems you have.  Points are great but sometimes there are blackout dates or the amount of points change.  It definitely pays to plan in advance.  I almost have a fail when I traveled to the Boston area during the Marathon weekend (though it was before).  The hotel told me it was a blackout date (though the terms mention that there are no blackout dates).  Anyways, I asked them nicely to let me use my points citing various reasons and they were able to help me out.

  4. ShannonRyan says

    Ugh, sorry to hear about traveling hacking woes. I definitely appreciate the rewards programs tied to my CC but I can’t say I actively travel hack, although I could see myself running into these same problems. It’s unfortunate but like you said, at least it didn’t end up costing you thousands. And now you’ve learned how to avoid these mistakes for your future trips, where it would have likely hurt your wallet more to experience them. Thanks for sharing your lessons with us!

  5. ferventfinance says

    I’ve learned you have to give travel hacking 100% to not get screwed. Therefore I’m very cautious and have been using the slow and steady approach. I’m not doing as well as most, but I don’t like over stretching myself. And at least you won’t make those little mistakes again!

  6. yvettedog says

    I’m not ready to travel hack yet. But thank-you for sharing this information. I didn’t know there was an airline called Sun Country. And when I’m ready, now I know to have extra miles.

  7. Jason @ The Butler Journal says

    I haven’t started travel hacking. I’ve been checking MYVegas since I plan on going to Vegas for my birthday in October. They definitely don’t have as much free rooms as they used to. That sucks.

  8. DC @ Young Adult Money says

    Jason@Islands of Investing The fact the programs can change so quickly is definitely a huge negative.  I’m all about learning from my mistakes!  I think some people are afraid to talk about their failures, but it’s part of life.  You have to embrace it and learn from it if you ever hope to succeed.

  9. DC @ Young Adult Money says

    Holly at ClubThrifty It’s not always easy to plan far in advance, though.  I’m all for 6-9 months, but honestly it’s not always realistic.  I think maybe 5-10 years down the road we’ll have more flexibility with our schedules, but we’re not at that stage in life yet.

  10. DC @ Young Adult Money says

    Andrew LivingRichCheaply Your friend sounds like he’s got travel hacking down!  It definitely helps to plan and be organized.  Nice job getting the dates worked out.  I think simply asking can go a long way.

  11. DC @ Young Adult Money says

    ShannonRyan It’s not easy to share failures, but I’m glad I did.  I think it’s important for bloggers to be transparent.  After all, no ones perfect!  And yes I’m very happy that this didn’t end up costing us thousands.  In retrospect it was a “cheap” lesson in travel hacking.

  12. DC @ Young Adult Money says

    ferventfinance I think it’s important to not stretch yourself too far when it comes to travel hacking.  I think talking to experts helps as well.  I plan on consulting my travel hacking “expert” friends for our Europe trip.

  13. DC @ Young Adult Money says

    yvettedog Sun Country is a great airline in my opinion!  If you ever fly to and from Minneapolis-St. Paul, I’d highly recommend seeing if they have flights.  They are virtually always the cheapest flights out there.

  14. DC @ Young Adult Money says

    Jason @ The Butler Journal The free rooms thing is terrible.  It really was the main reason I played, and it’s disappointing I won’t be able to cash in on them.

  15. mrandmrsbudgets says

    I’ve never played myVEGAS slots, but I really should start considering we go to Vegas 1x/year. Planning in advance is key to travel hacking especially for award flights. Turning cards like the Chase Sapphire Preferred and the Barclaycard are great cards because you don’t have to book through a specific airline or chain hotel.

  16. Lindsey at Sense says

    Thanks for sharing your travel hacking fail, it’s cool that you’re okay with sharing some of your financial fails. I know I always feel kind of stupid when I’m admitting my own faux pas on my blog but you’re right, it’s better to fail and learn from it than not do it at all. 
    I’ll check out Gary Vaynerchuk, I’m always look out for new learning opportunities. Cheers!

  17. Laurie TheFrugalFarmer says

    I think it’s great that you embrace your fails as a learning experience – that is SO important! Otherwise we just focus on the fail and not what wisdom we can glean from it!  We haven’t done travel hacking, just b/c we don’t want to open any more credit cards. One day, maybe, though. Great stuff here, DC. Thanks!

  18. DC @ Young Adult Money says

    mrandmrsbudgets Yep we’ve churned both those cards and still have our Chase Sapphire Preferred points to use.  Sun Country really is a great card to churn if you live in MPLS-St. Paul, though, because $500 isn’t much to spend within 3 months.

  19. DC @ Young Adult Money says

    Lindsey at Sense Honestly I think bloggers who never offer up failures are being fake.  We all have failures and I don’t think you lose legitimacy if you write about them.  Gary is awesome and I think at the very least he should provide you with some motivation.

  20. DC @ Young Adult Money says

    Laurie TheFrugalFarmer I’m still getting used to embracing failures but I think most people are WAY too fake about their failures/successes and I think a lot of bloggers avoid writing about their failures out of fear of how readers would react.  In reality I think readers really enjoy posts about failure because they can learn from them.

  21. houseoftre says

    Thanks for sharing your experience. I’ve never tried travel hacking & I’m sure I would make those mistakes. I tend to be a last minute booking person.

  22. DC @ Young Adult Money says

    houseoftre Yeah it was really unfortunate.  The myVEGAS slots thing was extremely disappointing.  I feel like I wasted a lot of time on it.

  23. blonde_finance says

    I hate that you had these travel hacking fails, but you totally made me realize a few things and open my eyes to potential drawbacks. We are in the process of travel hacking our way to Italy next summer and there are certainly a number of issues that could come our way and I want to make sure that I think through everything as much as I can before we pull the trigger on the trip.

  24. DC @ Young Adult Money says

    blonde_finance We are considering a travel hacking trip next Summer to Italy as well!  This experience definitely opened my eyes and made me think twice about how much time/effort I need to devote to travel hacking.  I also realized you always need contingency plans because sometimes reward programs change.

  25. Financial Tour Guide says

    We have a trip planned to Kauai this October. Thanks for the great info on some hacking fails.  We’ll be using some various credit card rewards to cover our trip and I’ll have to keep these tips in mind.

  26. DC @ Young Adult Money says

    Financial Tour Guide My advice on travel hacking: be careful.  It didn’t matter a whole lot for my relatively inexpensive trip to Hawaii, but if we are talking more expensive trips (like to Hawaii or Europe) you really want to make sure you have your ducks in a row.

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