How I landed a premium suite upgrade mid-way through my stay

One of the most coveted perks of hotel elite status is the chance to enjoy room upgrades — particularly suites. However, actually getting these upgrades isn't always easy.

Unless you're redeeming a confirmed upgrade certificate, you might need to do some sweet talking with the front desk or remind them of the hotel program's rules to get the upgrade you're entitled to when it's available. But even these strategies don't always work.

During a recent stay at the Las Vegas Hilton at Resorts World, I tried an oft-forgotten strategy: being flexible and trying again. And lo and behold, it worked.

When I arrived at the hotel, I checked in as usual. The agent thanked me for being a Hilton Honors Diamond elite (which I am through a cobranded Hilton credit card) but didn't mention any of my elite benefits.

I noticed there were lots of suites available online so I kindly asked if they had any upgrades to offer me. After all, Diamond elites are eligible for space-available upgrades, including suites. The agent was willing to upgrade me to a Strip-view room, but I was after a suite. So, I thanked the agent for the offer but asked if there were any suites available.

The agent explained that they normally only do one-category upgrades at this property but wrote down my nightly rate and length of my stay (four nights) and went to the back office to ask their supervisor.

Unfortunately, the agent said that they wouldn't be able to upgrade me at that time unless I paid the rate difference. However, because I was staying there for four nights, the agent suggested that I ask again throughout my stay as the property might be able to upgrade me later.

And that's exactly what I did.

Related: 6 tips to get the hotel room upgrades you deserve

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While the front desk agent the next day didn't entertain my upgrade request, the agent on day three did exactly what the first agent did — they wrote down my information and went to the back office. But this time, the agent came back with good news, saying that they'd be able to upgrade me for the remainder of my stay.

This wasn't just any upgrade either. While I was expecting an entry-level one-bedroom suite, I was handed a set of keys to a one-bedroom entertainment suite. The entertainment suite was about 400 square feet bigger than the standard suite and cost three times the price of my standard room. Score!

The takeaway here is that it doesn't hurt to ask for an upgrade midway through your stay when staying at a hotel for multiple nights.

The hotel might be sold out your first night but then wide-open the next. But even aside from that, the longer you stay at a hotel, the more you're spending there so if they have the space at some point in your stay, they may be happy to give it to you. In addition to a larger bill for the room, you're likely spending more on incidentals, such as restaurant purchases and spa services, too.

In my case, it was evident that the front desk agents were looking at my overall spending when deciding whether to upgrade me. In addition to looking at the room rate, the agent on day three saw that I had a couple of meals on-site, so that could have had something to do with my eventual upgrade.

Related: 5 ways Hilton Honors should improve its loyalty program

Bottom line

Some people might think it's annoying to switch rooms midstay. However, given that I got to enjoy two nights in the suite and didn't unpack much in my first room, I didn't mind. The sheer amount of extra space certainly made up for the relatively minor inconvenience of moving rooms. Plus, I got access to some additional amenities, such as a VIP lobby area with complimentary light refreshments.

Earlier this month, Hilton launched automatic pre-arrival upgrades for Gold and Diamond elites. Hopefully, this means that you won't have to wheedle your way to a suite going forward. However, if you still didn't get the upgrade you believe you're entitled to, there's no harm in trying this strategy on a future stay.