How to Win Travel Contests

By | November 16, 2019

How to Win Travel Contests

Over the years I have won some really great contests.  Amongst my friends it has become a joke: “How are you so lucky?”  Upon reflection, I am fairly confident that I do not possess some supernatural power.  Instead, I have some strategies that increase my likelihood of winning.  Today I am sharing with you my secrets so that you, too, can win contests.

Secret #1: You Can’t Win If You Don’t Play

My first secret is this: enter contests.  Hear me out.  You can’t win the prize if you don’t enter the contest.  I encourage friends to enter contests when I think it is winnable (more on what that means later).  However I have noticed, whether it out of inertia or disbelief, that often they don’t take the few moments to enter.

Secret #2: Get On Social Media

Most travel related companies have a strong presence on Twitter, Facebook, and Instagram.  These companies post their contests across their social media platforms.  Often the actual contest takes place on Twitter.

This week I won a free flight from Alaska Airlines during their ongoing #AlaskaHappyHour contest.  It took me about 30 seconds to enter the contest.  I’ve also won a free pool cabana for a day in Vegas, a bar set from Hyatt, iPhones, and other prizes through social media contests.

Secret #3: Enter Through Alternative Means

In the USA, law requires that contests offer the ability to enter with out purchase.  Most often, this is through a mail in entry, though sometimes it is done by sending an email.  Sometimes you are limited to one entry but often you can enter multiple times.

As I write this post, CLEAR, the service that allows you to hop the TSA lines at airports and quick access to sporting events, is running a contest for residents of the state of Washington.  The prize is a flight to LAX and tickets to an NFL game.  While the contest advertises entry by purchasing an annual CLEAR membership for $119, as an alternative you can mail in a postcard for the cost of a stamp.

Secret #4: Read The Fine Print

Make sure you follow the directions of the contest.  If it is a social media contest, make sure you include the correct hashtags.  Some mail entry contests require that you handwrite each entry.  If it says only one entry per person, only enter once.

A MasterCard and IHG contest a few years back allowed up to 94 mail in entries.  You first had to register for the promotion and then handwrite each entry.  Each entry needed to be mailed in separately though you were allowed to print the address.  While this took some time and the price of stamps, each entry was guaranteed a minimum of 500 IHG points.  I ended up with 50,000 IHG points and $150 in MasterCard gift cards.

Secret #5: Find Winnable Contests

The higher the barrier to entry and the smaller the population of eligible entrants are two key predictors to better odds of winning.

One of my favorite contest wins required submitting a short written response to why you should be picked as the winner.  The contest was only open to those living in a limited geographical area with a Delta SkyMiles number.

National contests for a large company where you can enter by liking a social media post are probably going to receive tens of thousands of entries.  Local contests that require a bit more to enter (sending in a postcard, coming up with a thoughtful response) still only take a few moments to enter but will get a fraction of the number of entries.

I have won trips to Hawaii, New York, and Europe through in person scavenger hunts in Seattle.  The barrier for winning was high — you had to physically get to a place in a short amount of time after deciphering a clue.  While you may not live in Seattle, there is likely some sort of contest near you that, with a bit of research and planning, is winnable.

Secret #6: Enter At The Start

Some contests have multiple prizes given away at multiple points over a period of time.  Often in these cases, if you don’t win the first prize, your entry rolls over to the next period.  You get multiple chances at a prize.

The other benefit of entering right at the beginning of the contest window when there are multiple entry periods is that the contest will not yet have as many entries.  Sometimes I set an alarm for the moment the contest begins so I can make sure I am one of the first to enter.  When the prize is given to the first person with a correct response or to arrive at a location, it is even more important to plan ahead.

Make sure you don’t enter BEFORE the contest has started.  This may lead to your entry being disqualified.

Secret #7: Don’t Get Discouraged When You Don’t Win

You aren’t going to win every time.  That’s okay.  There is always an element of luck with contests.  If you keep at it, and follow the advice in the post, you will increase your odds of hitting the jackpot sooner than later.

Most contests sponsored by hospitality companies are going to be legitimate as they have a reputation to uphold (not to mention legal ramifications).  Only once have I won a contest where the company (Virgin Hotels) never delivered on their prize.

Have you won a travel contest?  What advice do you have for others?

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