Should You Always Ask For Free Hotel Upgrades At Check-In? How?

While not playing into the “hack” side of it, in the US when I’m entitled to an upgrade at Marriotts I still need to ask for it. Sometimes even pointing out after I asked a first time that they’re still selling better rooms for tonight. I think you almost have to push a little now and advocate for your “benefits”

For years, my aunt has just engaged with the clerk at check in and been friendly, then discreetly slid a $20 or $50 bill across the counter "this is for you" and usually gets a somewhat nicer room. I've seen it happen a few times.

The "secret" insider information "hack" the hotel staff "hates" to share and doesn't want you to know about including your upgrades chances.

The "secret" is:
They don't give a f***.
They just want you out of their face ASAP.

I've been told 'no upgrades are available' so many times I just don't even ask anymore and take it as a pleasant surprise when they tell me 'we have an upgraded room for you' at check in.
Last time I was upgraded was in 2022 at the Hilton Saratoga Springs where I went from a standard room to a Junior Suite. I think it also helped that I was there during the off season for racing and when the pandemic was winding down.

Like you recently blogged about, most of the travel advice out there is these days is malarkey.

Being top-tier in the three major hotels brands, my best advise to get an upgrade is to actually stay at hotels which are not full (e.g. leisure destinations off-season) and non-business (typically, forget about it in London, Frankfurt, etc. where it's full of top-tiers)

I got fantastic upgrades (way beyond what I was entitled to) at the Hilton Dead Sea (Jordan), at the Hilton Batumi (Gerogia), etc.
On the other hand, I stayed 50 times at the Hilton Kensignton (London) and almost never received a meaningful upgrade (by meaningful upgrade I mean something else than the Hilton email saying that I've been upgraded to a room with a coffee table...)

I only broach the subject if they don't acknowledge my status.... any Diamond upgrades available? To be honest, most of my stays are at the mid-tier brands. On this Monday, my Hampton Inn for Friday already got upgraded to the best room they have available, which is one of the "& Suites" which usually means (since it's a newer property) the large desk down the middle of the room with a swivel TV and a sofa/chair/wet bar on opposite side from the bed. Which is more than fine by me... I like having the large table area. Being a Diamond rolling into a small town Hampton on a weekend is serious VIP...

In your example, Ben, of an aviation geek wanting an airport-view room, I don't see that so much as asking for an upgrade (though some airport hotels like that horrendous Stouffers Concourse, I mean Renaissance, at ATL try to charge a ton for it - then give me, a Bonvoy top tier who reserved such a room a 3rd floor room with a view of nothing but a tree and "sorry, it's on the airport side, it didn't say you'd see anything!"). I think phrased under something like that stands a better chance... I've asked before, having already for example scoped out the room maps on the Hilton app for a property, for an even number room on a higher floor - knowing this achieves what I want. They'll often do something like that without putting much thought into it.

I find it obnoxious when people who have zero entitlement to an upgrade either at hotel or on the train or with an airline ask/demand an upgrade. I always told my agents that if someone is being obnoxious about it or filming it like some social media "travel hack" (that'll make you wanna hack off a limb), calmly and politely explain that sorry, you cannot do that as those are reserved for our best repeat customers who give us significant loyalty.

The staff is well aware of your status. If they have a policy of upgrading whatever-status-you-have, they would have upgrade you with or without asking.

If you have to beg for an upgrade, it kinda goes against the idea of the hotel showing appreciation for your loyalty. The solution is to simply not book that hotel again.

Exactly, and I think this article is BS in that it just poo poos outright asking for an upgraded room and being confident and assertive, because that's not how Ben is. Rather, he's sheepish and introverted, so he doesn't have the balls to just ask, "Can you give me an upgraded room, since I see they're still available and I'm a diamond member." Most people respect polite confidence, not meekness and insecurity. I don't think any amount of schmoozing during a 2-minute check-in is going to be the solution.

But did the Instagram reel even call out not having status?

In my mind, I just read it as if you have status, this is the way you can ask for complimentary upgrades.

@ yoloswag420 -- Well based on the fact that the premise is an upsell vs. a complimentary upgrade, I think that's a safe assumption, no? At check-in, major hotel groups won't try to upsell you to a room that you're already eligible to be upgraded to (there are often paid upgrade opportunities in advance, but not at check-in).

@ MJ -- There's absolutely nothing wrong with that, and it is something I do. But that's not the premise here. The premise is getting a complimentary upgrade rather than getting an upsell. That wouldn't apply when we're talking about elite upgrades.

I'm not sure how true that is anymore, we've seen many data points showing that the major hotel chains are indeed trying to upsell you, with detailed stories of front desk staff trying to get people to buy up for cash, even with status that would offer it normally.

I just think for this archetype of content, I'd expect them to brag and insert something about how to get upgrades without even needing status as a way to engagement bait.

I honestly think on surface level, if you have status, this seems like fairly reasonable advice actually.

I mean, what would you expect from clickbait? If I also told you this one weird trick will turn you into a billionaire while making you 3 inches taller, would you believe me?

This isn't rocket science... If you want something in this world, ask. You'll either get it or you won't. If you don't get what you're asking for, don't be a jerk.

Keys to getting upgrades: Have status and stay in hotels outside the US.

This is not advice: I don't have upgrade eligibility at most hotels I stay at, but I get a fair number of upgrades (to just better or bigger rooms or views, only like twice ever to a suite). I haven't counted, but it feels like more than 40ish% of the time. I only stay internationally at about 5-10 hotels yearly. I don't know why I get them. I mainly book directly or through the Capital One portal (not the premium collection of hotels that offer an upgrade) My wife and kids are ok with us avoiding holidays and crowds and we strive to go hotels when they're empty. I never ask for an upgrade, but at check in I'm a talker (it's my nature). If I see that the front desk person is stressed I'll just say "has it been a busy day?" to start a usually longer conversation, or if they're happy I'll ask about their kids. Probably doesn't factor in, but I am happy with my upgrade percentage. Maybe it's just something else that's not either of these things, I have no idea.

Ask. Plain and simple. Be nice. Say please. Smile. Be prepared if they ask if you want to pay for a nicer room vs being given one for free. Don't eat yellow snow.

Our culture and economy has cultivated a sense of entitlement, or in other words a right for more for less (or nothing)… certainly becoming an increasing issue.

@Ash - I think you engaging with the front desk associates does help your odds at an upgrade. At more upscale hotels, staff are trained to be methodical and to follow set procedures for all guests. However, the front desk staff are still human, and at most hotels, if a staff member encounters a friendly guest who engages with them and makes them feel good, they may be more likely to check to see if they can do something for the guest to make their experience better.

I am also in the same boat, and I like to engage with others in the service industry when appropriate. Sometimes because I'm interested about them (like F/As and their stories), and other times just to make others feel a bit better. I have found that since I started doing this, I have gotten a lot better service, and more free stuff 🙂

@Luis. Fully agree! Lifetime Titanium here. In the US my upgrade typically is a “higher floor”.
At the Maldives: sunset overwater villa with a pool. In Barcelona, the most amazing suite I have ever stayed at the top of the hotel with an outside garden. I could list dozens of similar experiences.

What has created this culture of entitlement are the hotel loyalty programs themselves, which promise the world even to the lowest status levels members. If you tell me my status makes me eligible to upgrades, don’t be upset if I ask for one. If hotels were more honest and realistic about status benefits we wouldn’t be where we are.

My takeaway from all the comments: “How dare you try to upsell me, Mr. Marriott, when I’m upgrade eligible due to my status.”

Anyway, on a lighter note, we booked a room at the Taj Boston a few years ago on one of the discounter hotel sites (hotels tonight, or something like that, I can’t recall because we never go that route). Anyway, at checkin, I kindly inquired about a complimentary upgrade, and the kindlier desk clerk responded that with our fabulously low room rate that just wasn’t possible. We both enjoyed a good laugh.

I got a free upgrade at the Grand Hyatt SFO this summer. I have no status with Hyatt at all and booked a standard room with city view. At check in, my young son was checking out the planes in the distance, and I casually shared how my son is an AV geek. I honestly expected nothing, but check in agent said she found me a room with a view of the apron. We loved it!

Tl;Dr: having a cute kid might help. LOL!

This. Imagine being a front desk employee and having to say “no” over and over and over again. It’s not pleasant. Have some respect for their place in this.

I have 2600 lifetime nights at Marriott alone and can’t recall a single time I have asked for an upgrade. And of course, I have received hundreds upon hundreds of upgrades without asking.

@JB You're absolutely right, I get free stuff and even food from their own homes just by engaging, and it improves my experience significantly.

A few years ago, we paid cash (before I was into points and miles) for a hotel in Avalon, NJ. We booked a standard king room. We had never stayed there before. At check in, we were told we were being upgraded to a suite! I had no idea why! I literally was dancing down the hall because I knew what those rooms looked liked! Wrap around balcony facing the beach, kitchen, living room, and dining area! I was in heaven.
We also were upgraded this year when we stayed at a boutique hotel in Amsterdam. My husband asked why we got upgraded. They told us that when they have rooms available, they look to see who paid the most for their cash stay and those are the first people to get upgraded. I thought that was fair!