How to Score Free Upgrades When You Travel (Without Being a Jerk About It)

Here’s a true story: On my honeymoon, I walked up to the front desk of our hotel with a giant smile on my face, still in my wedding dress, and asked if there were any suite upgrades available. There were. And they promptly gave it to my husband’s best man.

That’s how extraordinarily bad I was at scoring free upgrades. It’s also direct proof that getting travel perks isn’t as cut-and-dry as “be nice.” I am nice, dammit. What’s the catch? I asked flight attendants, hotel clerks, Uber drivers, friends, friends of friends. I asked those mythological karmic beings who just cruise around sopping up life’s good graces. (We all know one. They make great travel partners.)

Turns out, there’s strategy involved in getting strangers to do things for you. You’ve got to be nice and you’ve got to speak the heck up. Be it a flight, a hotel, a ride, or a restaurant, you paid for this experience and you should be getting every benefit that you possibly can -- within reason. Here’s how it’s done.

There are two schools of thought here. One is, get to the airport early and chat up the gate agents. Once you’ve got a good thing going, ask if there are any upgrades available and you may end up at the top of the list. Even if the initial answer is no, they’ll remember you at the last minute should Joe Schmo in first class be indefinitely delayed.

Second school of thought: Ride the adrenaline high of a mad-dash through security, get to your gate at the last minute, then ask if there are any unfilled seats -- you may be able to claim a no-show’s forfeited seat that way. There’s also a chance the flight is overbooked. You’ll be moved to a later one and can request a first-class seat for the inconvenience.

Along those same lines, when your gate agent announces an overbooked flight -- which hardly ever happens, right -- be the chivalrous passenger who volunteers to wait it out at the bar for a later run. They’ll probably reward you with a first-class seat.

Rage against classist society all you like, but if you’re literally vying for admission into a higher class of service, it helps to look like you belong there. And they don’t wear spandex in biz class.
 

This is the person that first greets you when you set foot on the plane, also known as the purser. A recommended tip: Pick up some chocolate before boarding and hand it over as a thank you. At best, you’ll be on the good side of the person with the power to upgrade you to an empty first-class seat or give you a free glass of wine. At worst, you’ve given chocolate to someone with a very stressful job.
 

Let’s talk about “loyalty.” You know all those people getting on the plane before you, sitting in the good seats, sipping on their free drinks, just chillin'? They got there because they wisely flew around to a bunch of places for credit. If there’s one airline that flies out of your preferred airport that you wouldn’t mind taking on a regular basis, definitely do it. If their credit card will get you points and loyalty perks without plummeting your credit score, definitely do it. Points-based flight discounts and access to airport lounges alone is worth the effort, but while onboard, upgrades are typically given to loyal members first.

As it turns out, loyalty is an appreciated virtue pretty much anywhere you go. That story I told about my husband’s best man getting the Presidential Suite on our wedding night? (A suite so grand it came with an actual grand piano, by the way.) He didn’t even ask for it. He was gifted it because he traveled so much for business, and stayed at that particular hotel chain whenever possible. Do that, and eventually they just start giving you grand pianos.
 

We’re still on loyalty, but that’s because it works. Not just at big chains, either -- smaller boutique hotels and independent inns often have even more to offer, and a smaller pool of committed clientele vying for their perks. They’ll remember you.

The same logic follows for smaller airports. Rental car companies are more likely to notice that you’ve rented from that chain before, or a lot of times before, and will upgrade your vehicle for no reason other than they can.
 

I think it goes without saying, but if you book through a third-party discount site, don’t bother asking for anything. That goes for hotels, car rentals, and flights. You’re basically invisible to anyone with any power.

Ah yes, good old bribery. The “$20 trick” is a common piece of Vegas lore that has no reason not to apply at any hotel. Rumor stands, slip a $20 to the desk clerk checking you in and straight-up ask if there are any room upgrades or other deals available. It will go one of three ways: You’ll get an upgrade, you’ll get your $20 back, or you’ll get a “nope, but thanks.”
 

Tip your housekeeping staff, your bellboys, your everyone. If you’re a return customer or have to extend your trip, it’ll pay off. And if a hotel or restaurant does end up with a better room or table -- who are they going to give it to? That crazy old coot in room 7 who never tips? No, silly. It’s you!
 

If possible, don’t inquire about free stuff when other guests or customers can hear you. The hotel clerk, or whoever, knows that elementary school birthday party rules will apply: If they give one to you, they’ll have to give one to everybody.
 

Being honest about your experience requires you to be vocal about it. I don’t think I’m alone in having the instinct to just smile silently and trust that those in charge will know what I’m experiencing and compensate me accordingly. If your service is great, say so. If your hotel room has a funky smell or some doohickey on your flight is broken, definitely say so. Maybe a better alternative is available, or maybe, to make sure you’re a happy customer, the provider will go above and beyond. Complimentary drinks, baby.

If you’re celebrating an engagement or a honeymoon or an anniversary or graduation or birthday or literally anything, make sure you say it out loud. To everyone. Hotel clerks, Lyft drivers, bartenders, waiters, flight attendants (especially that lead attendant while you hand them their chocolate). There’s no harm in making conversation, right? And make sure that conversation includes a mention of why you’re very special and deserving of free shit.
 

For example, if you’re vacationing at a winery with your SO and you mention you’re looking for a wedding venue, you can probably expect some nicer-than-usual treatment. If you’re thinking of planning a big anniversary or birthday party at your favorite restaurant, make sure your waiter -- or even better, the manager -- hears about it the next time you’re having dinner.
 

Y’all, don’t say it’s your birthday if it’s not your birthday (especially at the airport, where everyone and their mother is looking at your ID). Faking an injury, death, or emergency to get a flight upgrade automatically makes you the scummiest person on the plane. Scummier than the dude who brought on McDonald’s and reclined his seat. And nearly every flight attendant, hotel employee, or wait staff I spoke to said they can tell when you’re lying. Just be a good person, m’kay?

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