The $20 Hotel Upgrade Trick

The twenty dollar upgrade trick is a nice way of gauging how far along you’ve come in the travel hacking game. I try it all the time whenever I check into a hotel and can say with confidence it works about 80% of the time. This is how it works:

When you check into a hotel, you slip the front desk attendant a $20 bill together with your credit card and casually ask them if there are any complimentary upgrades available. The unwritten rule is the desk attendant will confirm if there are better rooms they can bump you up to, and if none are available they give you back your tip. There’s really nothing to lose, that’s why it’s one of my best travel hacking tips!

I was a bit nervous doing it the first couple times, but I quickly realized there’s no need to be as it’s a fairly common practice in many hotels around the world. The Strip in Vegas is my favourite stomping ground; I’ve tried it with success at the Cosmopolitan, Bellagio, Venetian, Caesars Palace, MGM Grand – the $20 upgrade is practically a way of life there!

That’s why I usually book a basic room in any hotel I plan to stay; I know there’s a good chance I’ll get upgraded to the room I want for a fraction of the cost. A simple calculation will quickly show you it’s worth your while. For example, if a room upgrade costs you an extra $40/ night (that’s $280 for a week’s stay), I’d say a $20 tip well worth the risk of getting turned down.

How to approach it

Your success depends on your body language. You’ve got to come across as confident – show the desk clerk you’re serious by giving the tip upfront together with your card – but remember to smile and be specific about what you’re looking for (In Vegas, I always ask to be upgraded to a suite with a view of The Strip); you can say something like: “Hi. That’s for you;” as you slip them the tip. “I was wondering if you can upgrade me to one of your premier rooms with a view?”

My rule on small talk is to skip it if you can, although you’ll sometimes find desk clerks who prefer being talked up.

Be discreet

Make sure the Manager isn’t around, and don’t do it in front of the other customers; the desk attendant will not want to give the impression that he’s giving out freebies.

Other factors that help

Do your homework: of course, you’re more likely to get an upgrade if you know exactly what it is you’re looking for, so it pays to find out in advance the types of rooms offered by the hotel you’re planning to book. Checking out the hotel’s online reservation page is a good place to start.

Get your timing right: looking for a room later in the day gives the front desk a clearer picture of what occupancy will be like for that evening and the next couple of days. Turning up later improves your negotiating chances.

Try a recently opened hotel: customers are loyal to brands, so new hotels may find it difficult to prize them away from their regular spots. Hotels will sometimes go to great lengths to market themselves, in order to grow a dedicated client base. This is where you step in and take advantage any flexibility they may having regarding upgrades.

Mention it’s your birthday, anniversary or honeymoon: if it’s your birthday or you’re celebrating your wedding anniversary, don’t forget to mention it to the hotel agent as you pass them the $20 bill. Who wouldn’t want to be nice to you on your special day?

Raise the stakes: sometimes it helps to tip the odds in your favour; so if I’m staying a fancy 5-star hotel and want their best suite, I make a point of slipping them a $50.

My best $20 tip experience

I’ve tried the trick everywhere around the world – London, New York, Paris, Hong Kong, Miami, Rome, Hawaii, you name it – but my most memorable experience is our big family getaway in Mexico. We booked 6 basic rooms at a nice all-inclusive hotel (Moon Palace in Cancun). I’d done a little background check and new my chances of scoring were quite high. Upon check in, I slipped the hotel agent a twenty and politely asked if she could upgrade all 6 rooms to a top floor suite with an ocean view. I knew it was a big ask, so I put on my best smile. BAM! Just like that, it worked! We each got a big suite on the top floor directly overlooking the ocean. It made an amazing trip even more wonderful.

Why the $20 upgrade trick doesn’t always work

I’ve been turned down on room upgrades a number of times, but mostly it was because there were no upgrade rooms available. The attendants were polite most of the time when turning me down, and always gave me back my $20.

Sometimes all it takes to get a rejection is the wrong tone of voice – front desk clerks put in long shifts, which can at times put them on edge – so not being polite can be a real deal breaker. Sometimes you can miss the upgrade and lose out on your twenty – although it’s rare. Just remember, if you get turned down, to take it in your stride and move on!

The $20 upgrade trick is just one of the many travel hacking tips I’ve learnt on my 5-year journey. If you would like to learn more about collecting miles and points and travelling free, just sign up to my newsletter – I guarantee it will open up a whole new world for you, and you could win a few thousand points along the way!