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I keep reading about the $20 trick, i.e. slipping the desk clerk $20 when you check in to receive a room upgrade. Do this actually work or is it an urban myth?
We've heard countless variations on this story: Put a $20 bill between your ID and your credit card when you check in and ask if there are any "complimentary" upgrades available. It often turns out well.
But we've also heard of clerks who simply push the twenty back and indicate that they can't help -- possibly because there's nothing available, they have concerns over propriety, or house rules prohibit it.
There's another factor involved in these days of inflation everywhere: $20 might no longer be enough. It might get a clerk's attention, but perhaps not his or her undivided attention. Of course, a $50 probably would, but then you're in a place where, for that much money, you could've just booked the upgrade and avoided the hassle.
Also, for that kind of money, you can reserve a fully refundable rate directly from the hotel, rather than an OTA (online travel agency). Hotels like guests to book from them, since they get their money immediately and don't have to wait for the OTA to pay up. You often get much more attentive service by doing so.
It helps if you don't flaunt the tip and request. The last thing a front-desk employee wants is to have to try to upgrade a parade of guests, even if it means a bunch of twenties in his or her pocket.
Similarly, if you can time your arrival, the best time to check in is from 5 to 6 p.m. Front desks start getting crowded after 6, when clerks can become a little harried. Before 5, especially if check-in time starts at 4, too many rooms will be unavailable (still being cleaned), so you'll have to take what you can get. After around 8 p.m., too few rooms will be available and you'll have to take what you can get (i.e., no upgrades).
You can also ask to see your room in advance. This is sometimes dicey in Vegas hotels with thousands of rooms, especially if there's a line out the front door waiting to check in. Even if you don't ask to see your room upfront, if you can come up with a good enough reason that you'd like to change rooms, you can call the front desk, or show back up, and ask for a different room. You'll often be upgraded for your trouble.
If you're a frequent guest of the property and/or in a higher players club tier, you can go through the players club/host system without having to do any business with the front desk at all.
Are you there for a special occasion? We don't recommend making one up, but if it's your anniversary, second honeymoon, birthday, etc., you can mention it with your $20; the two combined often hit home with check-in agents.
It ultimately boils down to your chutzpah level and whether or not it will bother you to be declined. If it won't, then you have little to lose by trying.