Tipping at Checkin for Hotel Upgrades: in Las Vegas and Around the Country

twenty dollar trick las vegasThe Twenty Dollar Trick

Tipping for hotel upgrade: MleValue writes about tipping $20 at checkin at the Hilton Hawaiian Village. This is usually called “the twenty dollar trick”.  He got an ocean front Ali’i Tower room with free breakfast.

Personally I was surprised to learn that MileValue didn’t have Hilton HHonors Gold status, which would have gotten him free breakfast anyway (either this way or this way).

But $20 to upgrade his four night stay was clearly worth the ‘tip’ at checkin.

The only time I’ve ever done this is in Las Vegas.

When I was staying at the Bellagio for four nights I pre-prepared myself. I took out the credit card I would be using, and stuck a $100 bill behind it — folded so that it was smaller than the card, but with the largest ‘$100’ showing up so that it wouldn’t be missed.  This was a $100 trick rather than the twenty dollar trick.

I walked up to the check-in counter, pulled out my drivers license and the credit card (with $100 bill) now in my pocket, and slid it across the desk.

I was wondering if you have any upgrades available? I’d love one of those great big penthouse suites.

The usual advice is to pick a man over a woman at the front desk to check you in. I don’t know if that actually matters, but I hung back for a bit and watched the different checkin lines. Remember you don’t have to take ‘whoever is next’ to help you. Just hang back. I saw a woman who seemed to handle herself well, confidently. I didn’t want someone frazzled, overwhelmed. I wanted a veteran who wouldn’t be nervous, who would have been through this drill many times before.

The woman was indeed confident, but I got a little bit nervous when it turned out that the manager out front at the desk was hovering a few feet to her left. No matter. She noticed the $100 but barely blinked. Started typing away. Mind you, the Bellagio was booked solid even though it was July. She was having difficulty finding something suitable.

If all she had was a fountain view, I was prepared to swap out a $20. I wouldn’t have been happy with $100 for regular room with a view. And while if she had simply said ‘no’ I could have taken the bill back, I would have still tipped her $20 for trying. It wouldn’t have been expected, but I would have felt strange putting the $100 out there and giving her nothing, even if she gave me nothing, which probably goes to the ethics of the whole transaction.

After typing away for awhile she had success. A key lesson as well is to know what you want, I specified a penthouse suite and that’s what she gave me. It had two bedrooms and five bathrooms in addition to a dining area and a bar.

She said I’d like it, but did mention if I had any questions or concerns to please come back only to her (we didn’t want to involve anyone else in this little transaction of ours, did we?).

This was 2006, and I haven’t done it since. Even in Las Vegas, because I haven’t especially cared what room I had. (All of the rooms at the Cosmopolitan for instance were nice enough.)

I do think there’s something about Las Vegas which makes it ok. I know I felt ok doing it there, I also know I haven’t done it anywhere else. When you’re surreptitiously slipping a $100 to get what you want there you feel like Frank Sinatra. You feel like you fit in. That’s just how Vegas is supposed to work, right?

Sure, it’s engaging in a transaction where you’re paying a hotel employee to do something which may not be in their employer’s interest. You’re bribing that employee to sell you something at a discount, with them keeping the money instead of the hotel. That’s wrong, right?

It does feel wrong. At least anywhere but Vegas. And I’ve never had a great sense of how well it worked outside of Vegas, even though it seems to work most of the time in Vegas.

Very Good Points recently reviewed Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality by Jacob Tomsky. She didn’t like the book, describing it as “a detailed guide on how to hustle, steal, lie and rip off hotels and their guests.”

Tomsky is always talking about the value of tipping throughout — whether it’s what he would do for guests as a front desk agent in exchange for tips, or about the rest of the staff angling for tips, pressuring tips for guests, and how he would help them put guests in awkward situations so they would feel compelled to tip.

He began his career in New Orleans, and though he fictionalizes names he clearly started off working at the Ritz-Carlton there when that property opened. But his scamming didn’t begin until working at a hotel in New York.

New York is certainly a tipping town, and I suppose it shouldn’t surprise me how well tipping for a better room, free breakfast and late checkout works there at least in Tomsky’s telling. I enjoyed the book, even if it’s somewhat fictionalized, I read it over a couple of afternoons earlier in the month in Grand Cayman (hotel report forthcoming).

I didn’t want to know his experience of maids cleaning glasses with pledge, and I wouldn’t use his tricks to get everything free out of the minibar (when not staying at an Intercontinental). But I can still enjoy reading stories that horrify me.

And it got me thinking, how much can tipping get you outside of Vegas? How common is this? And how do I feel about it?  Have you tried a twenty dollar trick?

Me, I’ll stand by my usual approaches for securing the best hotel upgrades. Which includes tipping — in Las Vegas only.


About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Maybe Vegas is the exception, but generally this sounds like a race to the bottom. Extrapolate this further and you have to fork over cash in order to get anything done, with fewer upgrades for those that actually deserve them (frequent travelers). I have more self-respect than to try to bribe check-in clerks.

  2. I have no cumpunctions when it comes to discreetly ‘tipping ahead’ (bribe sounds a bit harsh), when I am in need of a nicer accomodation.

  3. that was 6.5 years ago. the $20 trick is well-known now. you don’t get those kinds of upgrades anymore. you’ll get a “strip view” or at bellagio, maybe a lakefront smoking room.

  4. I have to say, it never even occured to me that I should be tipping front desk staff, especially outside of Vegas. Though stories like this make me wonder if it’s happening more frequently than I realize. I’ve actually seen people tipping in Vegas even though they are usually trying to be discreet about it, but I’ve never noticed it anywhere else. Of course I suppose I wasn’t really looking for it though.

  5. I have used the $20.00 “sandwich” at the Bellagio which gave us a lovely room and floor upgrade. One more suggestion is to for the “front of the line” cards for restaurants, clubs or shows during check in.

  6. So, basically this whole thread is an apology of corruption. Bloggers have reached a new low,,,

  7. Cedric,

    Get a grip. The #20 trick is time honored and understood globally. I’m getting a little weary of the folks looking for any opportunity to dis travel bloggers. No one forces you to read these posts.

  8. I’m a Vegas regular and tip at every check-in. Now, I also tip everyone, every time while in Vegas, so I treat any bump as a bonus. My results have ranged from a high floor, better view to a 1,000+ sq ft suite w/270 view. I’ve had some clerks take the money and set it aside, and others hand it back to me immediately, but regardless of the “result” I always give them the tip. I read about some folks taking back the dough if the clerk cannot help them. I think that’s bogus.

    It’s Vegas…everything runs on tips. From the dealers to the cocktail servers to the doormen, you’ll have more fun in Vegas if you allocate a trip cost for tipping. Everyone’s happier and service is better… win-win.

    Lastly, you might check your Klout score. Palms is one casino that has admitted giving people bumps based on their Klout in hopes of positive social media feedback. Interesting.

  9. Mark, $20 tip for a better room is reasonable for them to keep even if they don’t help you, but $100? Would you expect them to keep it?

    Gary, I arrived at 11p at an Andaz in NYC and slipped the checkin iPad guy a $20 and he gave me a suite that was not going to be available on an award stay. Worked out very nicely…

  10. I read Gary’s blog to learn the “tricks of the trade.” I consider the $20 front desk tip a great new trick for me to try.

    Hotels are a service business. It makes perfect sense to tip the front desk.

  11. Milevale doesn’t understand elite status. Is he only united silver? And he thinks us miles are worth more than ua because he has no knowledge of what 1k benefits can do for you when booking an award. But hey, I’m sure he’ll boast about his free one way!

  12. I’ve used this trick in every city I’ve stayed in and, almost without exception, it’s worked. That includes recent stays in London and Berlin. In fact, in Berlin, they transferred me to a sister property that was a block away, but it was a “boutique” hotel with much nicer rooms.

  13. Bill,

    So in Vegas, do you give $20 to the dealer to get a better hand?

    Time honored or not, this is corruption. Further to the point, the guest here said he felt uncomfortable doing it right next to the manager. If it were so time-honored and widespread, then he would not feel that way.

    Merriam Webster for corruption:
    a : impairment of integrity, virtue, or moral principle : depravity
    b : decay, decomposition
    c : inducement to wrong by improper or unlawful means (as bribery)
    d : a departure from the original or from what is pure or correct

    Apology of corruption it is.

  14. Just because something is a time-honored practice does not make it not-wrong.

    The business loses revenue because an employee engages in unauthorized activity to give a patron something for which he/she is not entitled and the employee pockets the revenue.

    Perhaps if this was your business and you had an employee skimming revenue, you might feel differently…

  15. @Gary, MileValue mentions making a stack that included his Hilton Gold card, so I’m taking that to mean that he has status, but added the $20 “tip” anyway. I’m not sure how I feel about that… it’s probably harmless, but I worry about the precedent. I feel that as Hhonors Gold, if a reasonable upgrade is available it should be mine for the asking (published benefit). Are we sliding toward a system where the upgrade doesn’t happen unless I tip too? If MileValue had gotten a suite, which is not a published benefit, I could see that being worth the tip.

    Hmm. Now that I think about it, maybe the tip was irrelevant? Gold => free breakfast plus upgrade. MileValue should have gotten the exact same treatment without a tip… and maybe he would have. If I were the desk clerk, I wouldn’t turn down a free $20…

  16. Gary, Mlvalue clearly stated in the article that he has gold status with Hilton, and he presented the card along with his $20 tip at check-in. Maybe that is why he got the free breakfast. 🙂

  17. Cedric,

    No – but I give the dealer $20 when I have a nice win. Think “appropriate”. Where is the $20 trick appropriate?
    * Hotels (the room they upgrade you to is just as likely to go unsold by time of check-in)
    * Resturants – is tipping the maitre de for a better table corrupt?
    * Nightclubs – $20 can take you from loser to VIP with gaining admission through the velvet ropes
    * Theme Parks – so you can cut the line ahead of everyone else. NO! – Not appropriate


    It isn’t necessarily unauthorized, just not talked about. Believe me, if any real revenue was lost due to this, it would dissapear instantly. The fact that a clerk would accept the tip and upgrade someone near or in view of a manager says a lot. No one I’ve done this with ever showed athe least anxiety that they might be “caught”

  18. All I can say is, if I owned a hotel, any front desk employee caught doing this would be fired instantly. It’s theft, plain and simple. Any additional revenue associated with an upgrade belongs to the hotel, not to the front desk clerk!

  19. These comments are interesting, and I have a question. If the penthouse suite will go unused; because, no one who would pay is there for a period of time, then would it not be wise to assign it to someone willing to pay, in any amount, the room? In addition, this releases the standard room for someone who may not have planned ahead.

    I’m not sure I see a difference in the actual assignment, whether it is getting a penthouse suite in Vegas or a junior suite in Miami, which is made on the spot. Yes, money changed hands between the desk clerk and the patron, but the clerk had just as much power, ability, and right to assign the suites in either case. The tip just makes it personal for the clerk vice satisfying a DYKWIA.

    Here is a much more poignant example. Three Hilton Diamonds check into the Tropicana. One Diamond got status by spending $40,000 on a Hilton card (normal daily expenses for the year), the second Diamond got status by hotel hopping in Hampton Inns during a monthly 2 night trip each month for the year (with a couple of family vacation stays, including these to Vegas), and the third Diamond received status from 120+ nights per year due to extensive travel for work and staying in only Hilton properties. Which one most deserves the upgrade to the penthouse suite, and which one deserves it less? How would the desk clerk know that specific person deserves the upgrade over the others, especially over the least deserving? If the least deserving checks in first, should the desk clerk withhold the upgrade “just in case” someone more deserving arrives? In the end, a tie breaker is needed in this example, and since the desk clerk wouldn’t ask about a person’s history with Hilton, it stands to reason that a $100 tip makes for a viable tie breaker.

    Another question, it almost sounds as if the desk clerks should not be tipped, so is it ok to tip after the transaction is made? If the clerk receives a $100 tip after the room assignment is made, is it ok for them to say, “maybe we can do better than that” and redoes the transaction? Would it be wrong to hold the tip in plain sight during the transaction, so the patron wouldn’t need to fumble through their pockets afterwards (people do this with bell service and airline porters all the time)? Is it ok to pre-tip (give a larger tip early) maid service hoping for better service throughout the stay?

    What exactly are the boundaries that make a tip a bribe? While I don’t condone nefarious behavior, there are soft cultural boundaries that need to be recognized, which may fall in with the notion that it is ok in Vegas (or other places around the world). Remember, the advertisement “what happens in Vegas, stays in Vegas” is the city acknowledging and almost encouraging behavior that wouldn’t be seen as socially acceptable elsewhere in the United States, which makes it thrilling and fun in many ways.

    I’m just think’in 🙂

  20. I think this all depends on whether the hotel knows this is going on. If they know it happens and allow it to continue, then they have acquiesced to its occurrence and the employee is probably considered to have just receiving a tip like a maître de at a restaurant or a bouncer. If the hotel is actively trying to prevent this and employees continue to do it, this would constitute the crime of embezzlement/unjust enrichment.

    One question someone more knowledgeable than me will have to answer is whether this is just an assumed source of income for these employees. Perhaps the hotels know this happens and rather than try and fight it, they pay the employees less and accept that they will augment their income this way. I know a few places I have worked have done similar things since 1. It reduces the need to police a tough policy and 2. It saves the company a bunch of money in payroll taxes

  21. This post and the following comments do horrify me. Where do you draw the line.

    How about going $100 to a cashier to not charge you for bunch of items.

  22. –most everyone commenting here has probably been upgraded for no known reason. Thinking an upgrade comes directly from a tip is simply correlation not causation

    –the employee tucking the money is what every single employee who ever receives a tip SHOULD do. You don’t see high class service employees waving and counting their tips out in the open

    -judging ethics simply based on feelings is not a good litmus test

  23. with all the cameras around, hotel security and management can easily check if a front office employee was given a tip/bribe and it wouldn’t surprise me if that employee turned it in to the hotel.
    Assuming the hotels know about the practice and allow it, the IRS would be very interested to see if it is reported.

  24. @Dan (23): If you’re right, then this isn’t ripping off the hotel — but it is tax evasion. That’s still illegal and unethical.

  25. Do you really think that the hotels in Vegas don’t know that this is going on? They know everything that goes on in their hotels. These upgrades are all about putting people in a good mood and making them feel like they’ve “won” so that they’ll be inclined to spend more at the tables (where the real money is made). Who knows, maybe they pool all the tips and everyone gets a cut.

  26. C’mon people! It’s Vegas! The amount of tipping going on in that city at any given hour is astronomical. Tipping is the currency for almost every employee, from housekeeping to the blackjack tables to the strip clubs to the maitre’ds to the concierges to the valets to the…I could go on and on and on…

  27. Tipping is a custom in America. If you don’t believe me, just wait until the next holiday season. Log on to MSN and, I guarantee, you will see an article about how much to tip; the postal carrier, trash collector, doorman, dog-walkers, etc…
    Those posters getting on their moral high horses about “corruption” and the illegality of the tip are just bucking the system that has been in place for hundreds of years. Thus the use of the word “custom”.
    To address the pre-tip for a room upgrade… the hotels DO know about it (I’ve, actually, talked with a check-in clerk about it at the Bellagio), the hotel sets aside a block of rooms (unless completely booked) for “upgrades”. The hotel DO NOT lose money on this type of transaction. The penthouse (suite, upgrade, whatever)would have gone unoccupied anyway. The hotel still has the funds from the originally booked room. PLUS, now the person who received the upgrade will have a better outlook on that particular property and will tell their friends and family about “what a great deal” they received at that property. This gives the hotel great word-of-mouth and, quite possibly, a repeat customer. Win-win.
    If your personal ethics have a problem with this custom, it is completely within your rights to never tip and feel better about yourself. The rest of us will enjoy our better rooms and amenities without your approval.

  28. “Tip” is a euphemism here. “Bribe” is the correct word. Chris (#22), it’s a bribe when it comes BEFORE the (extra) service rendered. (The understanding it is the service will not be given without the bribe.)

    What seems to be clear is that the desk clerk must have the authority to hand out upgrades on his own, and for any reason. But, if he is falsifying the check in data in order to justify the upgrade (like saying you are a high roller even if you are not), then this is his problem.

  29. I have a feeling that the people who are horrified by the tipping have never worked in the service industry. In fact, I would wager a crisp $100 on it.

    I also read the book “Heads in Beds” and found it amusing (though exaggerated I am sure). And no, I don’t want to follow his ideas about stealing from the minibar.

    But if I want to give the front desk person a tip on my own volition to see if there’s something better available? There’s nothing that’s wrong with that. The person is friendly, helps me find a room that makes me happy, and I spend $100 more. The hotel doesn’t get it, but the hotel isn’t using all of their suites that night anyway — so it’s better to have someone say “I had the most AMAZING suite at the Palazzo/Cosmo/etc” to all of their friends and drum up business for the hotel, thus earning the hotel more money.

    Tipping is a thing. It’s not corruption. It’s not horrifying. If you don’t want to tip, don’t do it! You’ll get the room you booked and be just as happy.

    Tax evasion? Again, if you’ve worked in the service industry you report your tips on your taxes. Not reporting Gary’s $100 is like a bartender choosing to not report his $100 in nightly tips. It’s their own choice to defraud the government — you’re not complicit if that’s their “scheme”.

    And I agree with George as well — do you really think that the eyes in the sky don’t see what’s happening? In Vegas (if you ever tip) you notice that they often leave the money on the counter for a few minutes before they tuck it away. They don’t rush to put it in their pockets. If they were, then you may suspect something is amiss — but I would think that it would be a joke to believe that “management doesn’t know” (especially when the one who gave Gary the upgrade was standing next to a MOD).

    So, if you don’t think tipping is okay, then don’t tip anyone. But it’s probably one of the MORE ethical things that can be done when getting an upgrade (as opposed to Vanilla Reloads to the max, Amazon Payments or others — which I am not saying I am opposed to, just think about the things that we choose to do as point-chasers, and then think about how this actually hurts no one, and helps both you and a stranger).

    Everyone should have to work at least a year in the service industry. Seriously 🙂

  30. I was in Cancun and did not like the first room I got. I went back to front desk and manager came over as I had complained about the first room. I told him how about $100 for upgrade for my 7 night stay. He said that he could not take a tip for upgrade in front of the staff. Gave me a penthouse suite with his apologies and handwalk my luggage to the penthouse room where I offered the $100 again. And he quickly took it there. $100 did the trick

  31. Some data points, from personal experience:

    The cost of tipping/bribing (I’ll let you decide) in Vegas is going up, as the practice becomes more widespread. The days of $20 getting you a fabulous suite are over.

    There is no guarantee that $$ will lead to a better room than you would have received otherwise. I have had front desk agents pocket money and give me “upgrades” that were marginally better (if at all) than the room I had booked. (again, in Vegas)

    I had a roommate who worked at the front desk of a major downtown hotel in Chicago. He told me tips were rare, but that when he received them he did the best he could to accommodate their request. An upgrade to a view room, or club access, was doable. An upgrade to a large suite was not.

    I have yet to try $20 outside of Vegas, because it does not seem to be the custom / part of the culture. But from the comments here, maybe that’s exactly the reason why I should…

  32. I’ve never tried this for a room but when I would go out to bars and clubs I would be generous with tips. One reason was that I’m not a big drinker and I know the bartenders make most of the money off tips so if someone else would have drunk 2X or 3X the drinks I would have in the time I was taking up a seat at the bar I thought extra tipping would offset the different.

    In return I ended up getting exceeding well with anything from tickets to special events, numerous free drinks and occasional meals, etc. It also helped that I was low maintenance.

  33. How about if I tip the airline gate agents? Will it work? If so, how much and how much upgrade? Economy to Economy plus, Economy to business?

  34. I used to travel with a €100 note tucked inside my passport sleeve as emergency money. Once while leaving Germany, an immigration officer found it. He nonchalantly handed it back to me, saying “I don’t need it.” I no longer keep money in my passport sleeve.

  35. I used the $20 at the Hyatt Regency SF recently and got a suite because of it. It was a one night stay and the guy was thrilled when he saw the $20 under my credit card.

  36. We recently tipped and got a nice room at a Marriott in new Orleans. Totally worth it since the room was covered by my employer anyway!

  37. Definitely considering this for an upcoming stay in the Caribbean at a Hyatt, have a week stay as a Diamond in a club room already, however I know this particular property is rather competitive, wondering if it is worth the outlay or not.

  38. Frankly this practice disgusts me. Its corruption in its purest form: The employee takes a personal tip and offers company resources in return. That is nothing less than stealing from your employer.

    Tipping is fine. Getting a room upgrade is fine too. Even using some promotion or credit-card signup to earn miles for almost nothing, while spending them on the most luxurious properties is fine. Because that is all while following the rules.

    However an employee giving you an upgrade which is costs the hotel money (Using a larger room is more expensive, and money is lost of that room otherwise may have been sold to a paying customer) is simply corruption, and that employee should be fired. Vegas or not.

  39. Damn, I had a nice speech all written in my head, but Jane stole it and put it even better. And, the last line is definitely true. Tx, Jane.

    Does anyone know if this is how it works in HongKong? I have a trip coming up there and would love a room with a view (it’s Hyatt, and I’m already diamond and using suite upgrade, so . . . .).

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