Playing Vacation Roulette

I’ve been spending hours lately looking for last-minute options for a spring break getaway (instead of writing blog posts…sorry).  Essentially, I have a paid holiday at work burning a hole in my pocket as an excuse to travel, and have waited far too long to actually book something.  What I’m left with is a large supply of Delta miles that won’t get me anywhere but Montreal or Rapid City at the low level and Membership Rewards points that look more promising through last-minute no-fee redemption with Avios or ANA miles.

Despite having some options, I kind of have my heart set on heading to Central America for Semana Santa.  The only problem?  Apparently everyone else does too (at least based on the lack of award availability).  Cash prices are also on the high side, so I started looking for ways to help bring down the cost.

Get Going is Google Flights with a twist.  It offers exactly how I start my travel planning: enter a specific departure airport and specific dates but leave the destination very much open-ended, with options such as “Europe” or “Beaches & Sun”.  For me, this is a great way to look for deals since my dates are usually set in stone making ITA searches only semi-useful for inspiration.

The reason Get Going trumps other search options is because it doesn’t just show you flight prices.  It shows you discounted flights.  Through ITA, the cheapest flight I can find to GUA on my specified dates is $693 – and that’s an awful flight with a forced overnight in Miami (essentially undoing my specific date request).  The cheapest flight that I’d actually book is $734.  Ouch!

Get Going, on the other hand, offers the exact same flight for $538.

So what’s the catch?  (And yes, there is a catch).  For one thing, you don’t *officially* know which airline or flights you’ll be on.  Unofficially, all of the potential flights I looked at were really easy to discern, so I wouldn’t worry too much about that.  The bigger trade-off here is that you’re trading off a whole lot of flexibility, including your final destination.

In order to take advantage of these lower prices, you actually have to give Get Going two choices for your vacation.  In other words, I can’t just tell them I want to book a trip to Guatemala: I have to say I’m content with getting either to Guatemala or Panama (for example), and Get Going will call the final coin flip for you.

The good news is you can pick both of these options and have pretty good insight into which flights you’ll be offered.  The bad news is you have to be 100% flexible on which of these two destinations you end up at.  In fact, you’ll authorize your credit card to be charged before finding out which tickets have been booked, similar to bidding on Name-Your-Own-Price travel arrangements with

If you’re honestly happy with a 50/50 chance of getting either destination (as I often am), this can be a good way to lock in some cash savings.  It truly is playing vacation roulette, except you win either way.  Risks are minimized, since you know in advance when you’ll be facing 3-connection itineraries, overnight stopovers, or alternate airports.

Frankly, the savings aren’t quite as good as they may appear.  In this particular example, there are clear cash savings of $170+.  However, in the process, I’m forfeiting roughly 2% in shopping portal bonuses and perhaps another ~$80 in airline miles (since Get Going does not guarantee you’ll be booked into a mileage-earning fare class).  Am I still money ahead?  Yes, in this particular example, but if the savings from Get Going are lower, you may find yourself better off booking directly.  There are other things to consider as well.  Even if the savings ended up negating each other, you may prefer a cash discount now compared to miles you can redeem later or vice versa – depending on how you value airline miles and your typical redemptions.  Or perhaps you prefer to book directly for greater flexibility in ticket changes or cancellations.

I am honestly considering giving this a try, if only for the excitement and mystery.  Given that I’m looking at booking only two weeks in advance, some of the disadvantages become moot points for me.  I know I won’t need to cancel my flights, I know I’d be happy in either destination (or even a dozen others), and I can rest comfortably that the flight times are convenient for me.  I’m willing to take my chances with a discounted ticket.  Of course, the rational part of me says to use my airline miles, but Get Going wins in convenience of not having to search over and over again to find an available seat…

What do you think?  Should I play vacation roulette?

If you’re interested, you can earn $25 in Get Going credits by joining via my referral link and your Facebook account.  Joining through this method also nets me a referral credit if you decide to book a flight within 90 days of joining.  I am always grateful for your support of my blog, but I’d also encourage you to share your own referral credits in the comments below and/or join through a reader’s link.  Sharing is a huge part of the travel community, so help your fellow readers out!

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Editor and Lead Author at The Girl and Globe
Becky loves hiking and the outdoors, reading a good book on a rainy day, practicing yoga with friends, cooking with Sinatra in the background, relaxing with her husband and a good glass of wine, and above all: travel. Read more about Becky.


  1. Missy Hellendale says

    Fascinating, thank you, more new stuff all the time. I may give it a try. If you end up in Panama I can lend you my apartment in the city (I’m stuck in the US until June). I enjoy your blog.

  2. D. Griffis says

    Hola! If u hvnt been to Panama n u end up there n u want GUA, then u btr chk wx. If u chose to go by land then u get a bus. I wouldnt advise renting a car unless 1) its a 4WD. 2) The roads n bridges arent washed out or being repaired. 3) U know exactly where ur going & arent afraid of some very shady characters. 4) U sometimes are buying gas frm an outhouse and 5 gal. cans.
    Now if u go by plane u want to fly in a.m. Bcuz going over mountains in p.m. in a regional, usually 1 engine is like riding a rollercoaster. But then either way ur not saving $$$.
    Just saying frm exp.

  3. says

    @Missy, that’s a very generous offer!

    @D. Griffis, thanks for the advice. I definitely wouldn’t be renting a car.

    @Kay, amazingly nothing to MEX at the low level. Ironically, it was one of the first places I tried.

    @The Deal Mommy, thanks for the vote. Have to decide something soon whether it’s spinning or miles or I’ll be stuck at home!

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