Last month, I used 145,000 Hilton points to book a four night stay at the Hilton Hawaiian Village in Waikiki. (This was a 55,000 point discount because I booked an AXON award.)

When I booked, the only room available was one king bed. My traveling party wanted two beds, but I wasn’t worried because I knew that would be an easy change at check in. My other big plan for check in was to use the Twenty Dollar Trick, which I first learned about from thetwentydollartrick.com.

The website is a repository of data points for people trying the Twenty Dollar Trick in Las Vegas. Here’s how the trick is described:

“The twenty dollar bill trick is sweeping the travel industry and becoming extremely popular, especially in Las Vegas. When you check into a hotel you simply slip the front desk clerk a $20 bill with your credit card, while asking, ‘Do you have any complimentary upgrades available?’ The general rule of thumb is that the front desk clerk will check for upgrades and if they cannot find anything they will return the $20 tip, making it risk free!”

I’ve known about the trick for years, but I haven’t tried it in Vegas. Last month my friend tried it at the Cosmopolitan and got upgraded from a standard room to an incredible suite with a bathroom with windows onto the strip and a bar for the weekend. For $20.

I was eager to try to the trick at the Hilton Hawaiian Village.

The Conversation

As I walked up to the check in desk, I made a stack. At the top was my Hilton Gold card. Below that was my driver’s license. Under that was a folded $20 bill. At the bottom was my credit card.

By chance our agent was a guy in his twenties. I thought that was a good sign, but who knows.

I think the wording of the trick is so awkward. “Do you have any complimentary upgrades available (while I bribe you)?” So I reworded it slightly to include my other request for two beds.

I handed the agent my stack and said, “Do you have any complimentary upgrades to a room with two beds available?”

He noticed the $20 bill and threw it behind his keyboard where no one could see it. I knew that was a good sign. He said, “I’ll see what we have available.”

He said that there was an ocean front room available in the Ali’i Tower. That sounded good. He also said he could get us free breakfast. That sounded good too.

We took the keys and went to the room, and we immediately realized how much that $20 had bought us. We were on the second highest floor of the Ali’i Tower looking straight out at the ocean. The view on the background of my twitter account (@MileValue) was our view from the room.

Beyond the view, the Ali’i Tower had several benefits. We had access to a private pool for tower members only, which was much less crowded than the resorts other pools. The pool had incredible beach views.

The tower had a DVD and Playstation 3 game kiosk where tower members could borrow a disk at a time for free. This should have been a nice benefit, but we borrowed The Campaign, which is awful.

The tower had free tea and coffee in the room, which was a nice morning benefit.

For a random weekday in October, Hilton Hawaiian Village is charging $239 for the base room that we would have gotten and $449 for the room we did get with free breakfast. Over four nights, that’s an $840 upgrade for $20.

Or I could have redeemed 111,719 points for one night in the room. I got four nights for 145,000 points and $20.

I’m not saying that I got $840 in value from the $20 trick. I slept through breakfast, though my friends liked it, and the view was not worth $160 per day. But I did get far more than $20 worth of value.

Is it Repeatable?

Yes. Here’s the data from Las Vegas. 84.4% of reports are of a success. Of course, success is relative. Some upgrades are minor, and some are major. But even a minor upgrade is worth $20, especially if you are staying several nights. And I also imagine there is a self-selection bias whereby people are more likely to report successes. However it’s clear the $20 trick works in Las Vegas and beyond.

Is it Ethical?

It does look like the guest and employee are circumventing the hotel’s ability to profit from its best rooms. But on the other hand, hotels give their check-in agent huge discretion over where to put you.

I can’t tell you whether the Twenty Dollar Trick is ethical, but I welcome civil debate in the comments (and will mercilessly delete unconstructive negativity toward any person.)

Recap

Slip the person at the front desk a $20 sandwich, and you may find your next hotel stay vastly improved.

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