How to Land Posh Hotel Upgrades for $20

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Frugality gets a bad rap. While it's not as bad as being "cheap," frugality is often seen as going hand in hand with a life free of luxury and a disdain for all nice things. And while my husband and I try our best to live frugally, we also like nice things. So when describing our spending philosophy, we prefer the term "money savvy." Money savviness means getting more for our money, whereas frugality often equates to just spending less. And one of our favorite ways to be money savvy is the $20 hotel trick.

What if I told you that you could get a deal on your hotel room, and for a mere $20, you could also get a swanky upgrade? Well, I just told you. And it's as awesome as it sounds.

The $20 hotel trick is geared for hotels with premium rooms (think four- and five-star resorts) in major vacation destination cities. The tactic is most commonly in Las Vegas, but other cities like New York, Los Angeles, Chicago and Atlantic City may have prime hotels where you'll find success. Here's how to score your upgrade:
  1. Search for hotels in your destination city that have great deals on standard rooms and also have upgrade options. Remember, you want to pay for an average room and get upgraded to an awesome room. And if you're really feeling frugal savvy, save a few more bucks by using Priceline Negotiator or Hotwire and use these tips to book your hotel.
  2. Upon arriving at the hotel, prepare your "$20 sandwich." Take a folded $20 bill and slide it between a credit card (on top) and your driver's license (on the bottom). Others prefer to simply wrap their credit card with a $20 bill, but we prefer to be more discreet. After you've constructed your sandwich, place it in your pocket.
  3. Go to the front desk to check in. We do our best to act friendly and warm with the desk attendant to start things on the right foot. During the check-in, we hand the desk attendant our $20 sandwich and ask if there are any complimentary upgrades available.
  4. Now it's time to await the verdict. If everything works right, the attendant will hack away on the computer for a few moments and let you know that today's your lucky day and an upgrade is available -- while slipping the $20 bill in a pocket. And if you're not so lucky? The attendant will slide your card and unaccepted Andrew Jackson back across the desk. No harm, no foul, but no upgrade either.
So why doesn't it work all the time? There are lots of reasons, the most common being that there aren't any upgraded rooms available. You're less likely to succeed on busy weekends or holidays. And while many hotels encourage employees to upgrade guests at their own discretion (compensated or not), others have policies that discourage them from pocketing tips.

We've gone three for three with our attempts in Vegas, averaging over $75 a night in upgraded room savings. You can see how other travelers have fared. While results vary, there are enough success stories that end in penthouse suites to convince even the most timid to give it a shot.

Have you tried the $20 hotel trick? Any pointers or success stories you'd care to impart? Let us know whether or not you have the stomach to serve up a $20 sandwich.

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I really would like to see this couple write something that is actually helpful --- instead of making a habit of bragging about their many vacation trips.

Also, I agree with other comments that have been posted that this latest "savvy" travel advice of theirs is definitely borderline slimy. It doesn't just "sound" sleazy. It is.

June 24 2014 at 5:21 PM Report abuse rate up rate down Reply
1 reply to Valerie's comment

ovomit n his lard arse american hatin wife ,take vaca after vaca on all americans dime while they both drove america into the crapper.!!!!

June 24 2014 at 7:53 PM Report abuse -2 rate up rate down Reply
Tracy Wiswall

Having worked the desk in a hotel for a few years during my college days and traveled extensively for work since then...I can tell you hotels are a strange business. Tips are expected, upgrades are always negotiable, and much of running of the hotel is left to the employees not the managers. So while it sounds sleazy...and could be against the policies of some (bribes if you want to call it that) are just a commonplace activity in that business. Same goes for restaurants...$20 can often get you a better table...or a reservation when there is no availability...of course a C-note usually works better at both locations. ;-)

June 24 2014 at 1:52 PM Report abuse +1 rate up rate down Reply

So you're encouraging hotel employees to steal revenue?

Slimey, at best and likely illegal, as well as a way to get employees fired (there ARE security cameras on almost all hotel desks, you know).

June 24 2014 at 12:58 PM Report abuse +5 rate up rate down Reply

I don't mean to sound like a prude, and I hope I am not one, but isn't that kind of a tawdry bribe? How about just acting decently toward the desk clerk and ask if there is any upgrade available? This may work in many third-world countries, and even sometimes in the US, but I am leery of participating in a cheap stunt that demeans both the clerk and the guest.

June 24 2014 at 12:42 PM Report abuse +4 rate up rate down Reply