How To Score An Upgrade - Hotel Confidential

Welcome to the latest edition of Hotel Confidential, a monthly series exploring the inner workings of great hotels. This month's topic is one I know everyone can appreciate... Scoring the free upgrade.

"It looks like we have a nice upgrade for you this evening."

These are truly the most beautiful words in the English language. Nevermind "I love you" or "Why don't you come inside for dessert," nothing brings music to the ears quite like being told you've scored a free upgrade at a hotel. Not even hearing the late Rod Roddy announce "Come On Down!" could get the blood pumping quite like these sweet nothings from a front desk agent.
Those little balconies are the suites...I know from experience.

Free upgrades at hotels are like a drug, and during my tenure behind the front desk I witnessed countless guests try to lie, cheat, and steal their way into a fix. Some were successful, while others were sent away to their standard double queen room; the assurance of a "very nice view" offering little relief for their withdrawal induced shivers.

The guests that were successful in scoring the upgrade - without offering their first born child - usually had the same things in common which unlocked the gates of heaven. There are also a few sure fire ways to ensure you'll never see the inside of a concierge lounge without paying for it. Want to know what they all are? Well, you've come to the right place...
Once you have had all this, it's hard to go back...

The Do's

Call the front desk

A day or two before your arrival, call the hotel and ask to speak to the front desk. Some properties avoid transferring calls there at all costs, so you'll need a good excuse as to why you should be put through. My suggestion: call during the evening shift (3pm-11pm) and say you'll be arriving to the hotel in the morning, and wanted to find out the possibility of an early check-in. That should do the trick...

Assuming you get through to the front desk, stick to the early check-in story for a bit, but this is just part of the set up. Before the conversation ends, simply ask the agent "What sort of room did they reserve me?" If you're really lucky - I mean once in a blue moon lucky - they just might bump you up right then. This has happened to me twice as a guest, but don't count on it for scoring your upgrade. The real reason you've called is to make a connection with the desk agent who will quite possibly check you in tomorrow...
Never forget who holds the keys to your upgrade...

Be nice

Remember that old saying about honey and flies? It's lame, but true. If you walk in the lobby with a crummy attitude thanks to your 9 hours of travel, there is a better chance of the Cubs winning back-to-back World Series than you scoring an upgrade. You're probably the 67th check-in the desk agent has processed today, and guess what? The vast majority have shared how lousy their day has been. Smile...compliment the hotel...make small talk with the agent. Do what every other guest doesn't do and you just might be rewarded.

This is also where your phone call the prior day can come in handy. You remembered the name of the agent you spoke to, right? If they're working, do what you can to make sure they're the one to check you in. If you're successful, here's where you toss out a "Oh, So-And-So! I talked to you on the phone yesterday, thank you so much for your help!" Again, no guarantee this gets you anywhere, but it definitely can't hurt...
They don't care about your flight...the other 53 people had a bad one too...

Try and pay for it

Ask anyone with frequent success landing an upgrade, and they'll probably tell you the most effective way is to simply ask for it. Sure, this will no doubt work some of the time, but there's a better way to go about it that doesn't make you look like the rest of those in search of something for nothing.

During the course of check-in, inquire with the agent what the rate would be for the upgrade you desire. After they share with you the new rate, decline it by saying something to the effect of "That's OK, I won't be in the room that much anyway. Thanks for looking for me though." Because you offered to pay for it first - unlike 99.9% of those that ask about an upgrade - you may find the agent decides to give it to you anyway...
Sometimes if you offer to pay for the ocean-view, you'll get it for free...

Arrive really early or really late

When pickings are slim for available guest rooms, your chance of landing an upgrade goes up considerably. If you arrive to the hotel early in the morning, and the only room left clean from the night before just happens to be a suite, there's a good chance the hotel will elect to give it to you rather than have you wait. Same thing goes if you arrive very late in the evening and the hotel is fully booked. In this case, the last one in sometimes gets the best room in house. 

If these tips don't work, there are two other options to earn an upgrade, but they're not nearly as fun. You could invest around 40 nights of your life each year with a chain and earn top-tier status in their loyalty program, or even more effective, you could pay for it...

The downside to checking in at Midnight is only having 8 hours with a wet bar.

The Don'ts

The $20 Trick

In Las Vegas, the practice of slipping a $20 to the desk agent in exchange for an upgrade has more or less become a widely accepted form of bribery. It's Vegas, so I'm happy to give those that try "the $20 trick" a free pass, but it should never be used outside the limits of Sin City. It's degrading to the person behind the desk, and they shouldn't be forced to choose between their integrity, or a few extra days of gas money. Not to mention that down the road, karma will probably tax you the money you saved and then some...
Just because it works here, doesn't mean you should try the $20 trick everywhere.

The Loyalty/Credit Card Combo

Congratulations, you've received your gold loyalty card in the mail. Do you have any idea what this means? That's right....nothing. There is no need to strategically place this worthless piece of plastic on top of your credit card, so the desk agent is sure to see your less than illustrious status. They already have your number on file from the four different places you decided to share it in your reservation. What they will need, however, is your last name, unless of course it really is 495680321. 

By the way, you know who doesn't try this ploy to earn an upgrade? Platinum and Diamond members....the one's with actual status. Well, most of the time anyway; there are a few that still need the self esteem boost.
This is all that shiny new card gets you....water.

All of these tips for scoring an upgrade in a hotel come with a few assumptions. First off, if you are staying for multiple nights then your chances of landing a free upgrade plummet, regardless of what tips you may try. Hotels will rarely upgrade someone for more than one night, unless they are a Platinum member, or severely overbooked on a particular room category for several nights in a row. 

The other assumption is that the desk agents at your hotel are actually empowered to upgrade guests. At larger hotels, guests are often assigned a room in advance, and the front desk has little liberty in making a change. That is, without the help of supervisor, but now you've already wasted your charm and "how much is an upgrade" strategy. The resorts at Disney are a perfect example, where it seems that any room changes must first be approved by CEO Bob Iger.
If there's a roped line for check-in, you're probably not getting an upgrade.

Regardless of what tips you may try, scoring an upgrade at a hotel requires one thing more than any other...luck. If you should find yourself soaking in the jacuzzi tub of the awesome suite you landed at check-in, try to keep a little bit of perspective. More than likely it won't be like this next time, and kicking the addiction to free upgrades is easier said than done.

Enjoy Your Stay

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