This post is part 2 of 3 of a segment regarding recompense in a travel situation and making a powerful and ultimately successful Ask, with the reasons and benefits.


Everybody appreciates free benefits and perks. If you’re celebrating something special, or have some pressing circumstances, you can and should reach for perks from hotels and airlines. My previous article (How to Get Freebies Without Being a Jerk) touched upon how to ask for benefits or compensation when something doesn’t go quite right.

But what if everything goes smoothly? How can you improve your experience then?

It’s simple. Just convey to the hotel or airline the importance or significance of that trip. They would typically be more flexible and willing to assist you in making your experience the best it can possibly be.



There are a wide variety of reasons that they should upgrade your time spent with their service. There are of course the major and common ones:

  • Birthday
  • Anniversary
  • Celebration (Wedding, Graduation, etc.)
  • Loyalty (Hotel or Airline status benefits)


Some additional (and true!) examples that I have used for an Ask include:

First time in a Westin, they made my experience memorable.

First time in a Westin! Courtesy of Starwood Hotels

  • Visiting with my significant other’s parents and need to make a great impression (yes, it’s true!)
  • First stay after hitting Gold status
  • First stay after hitting Platinum status
  • Chasing status
  • Repeat trip to the same property
  • First time in specific class of hotels
  • Booking for family / parents / etc.


Keep in mind, like the previous article mentioned, be reasonable and prudent in your Ask. Don’t ask for the moon, but emphasize your loyalty and more specifically but subtly note what you can do for them. Don’t lie or embellish, be truthful, lest these companies scale back their generosity. I think of my travels, especially in the hotel business, as a give and take relationship. They are willing to go above and beyond for me, and I am grateful and make sure that is communicated. This will be further detailed in the next post.



Here, it pays to be knowledgeable and do your due diligence. Be specific in what you can ask, or let them suggest some option and steer them towards what you want.

Some examples of benefits I obtained include:

  • Room upgrade – from a standard room, to a suite! (Or better?)
  • Free breakfast (continental AND a la carte), lunch, or appetizers (for the whole party)
  • Free drinks (for the whole party)
  • Late checkout – even in high demand, everyone-must-be-out-by-noon days
  • First Class seat upgrade
  • Free valet parking – which for some major city hotels can hit $50 or more!
  • Complimentary champagne, fruits, candies, cakes. Excellent, especially as a surprise!


Some argument could be made that I should have gotten some of those benefits regardless (such as free drinks, for my SPG Gold status). While this is true, I am usually able to get that standard benefit in combination with other perks, such as free breakfast, room upgrade, AND reward points. Typically guests only choose one benefit, which is limited to a maximum of two guests. By being cordial and friendly, they are inclined to grant you the benefit for the entire party.

Please note: if you’ve never stayed there before, or have no status with the hotel chain or airline, asking for some or all of these will most likely be declined. Try for one, and see how that conversation goes. Leverage your loyalty to get the most of your experience.


The next and last post in the Art of the Ask series will conclude with some behind-the-scenes analysis, and provide easy to understand activities to engage the hospitality employees, in pursuit of those benefits.


Featured Image from Starwood Hotel Website.

Have you Asked successfully before? Let me know what perks you got! Post below in the comments, or reach me directly at! Like my posts? See more here, on TravelUpdate! Follow me on Facebook (The Hotelion) or on Twitter and Instagram@TheHotelion

Read more: How to Get Freebies Without Being a Jerk