Basically, you tip the desk clerk for a room upgrade. But there’s a science to it. Well, a “science.” It goes like this.
When you sidle up to the check-in desk at your hotel, you’ll be asked to present your credit card and ID, like always. Slip a folded $20 bill between the two, and casually hand the bundle to the front desk manager while politely asking, “Do you have any complimentary upgrades available?”
That complimentary part is key. You’re not paying for the upgrade. You’re simply paying for the worker’s effort and consideration. With a little luck, they’ll find you a nicer room, pocket the money and everyone wins.
So does it work? I’m two for two, with successes at a boutique hotel in Chicago and an upscale chain in Mexico City. The former resulted in moving from a standard room to a junior suite—so a significantly bigger room—on a higher floor and with a better view. The latter meant moving from a standard room to an executive suite, which gained me access to the executive lounge and all the free drinks that entailed. In each case, I’d estimate the upgrades for my three-night stays falling in the $50 to $75 per night range.
Sure, it’s hard not to feel self-conscious when slipping unsolicited cash into someone’s hand and hoping for a tacit nod signaling that you two are, in fact, on the same page. In my case, the $20 handoff was pretty anticlimactic—both were simply acknowledged with a small smile and something akin to “I’d be happy to check on that for you, sir.” But what if your tip is rebuffed? What if there’s a strict policy against taking bribes? What if the clerk only complies for $100s? But the risk is low—worst case, you lose a little money—and the upside is high. Because depending on the particular desk clerk (and hotel inventory), you might wind up spending a few nights in the penthouse suite for the additional price of room service toast.