My experience trying for an upgrade — UNSUCCESSFUL

Last week I wrote about the things I look for when booking a hotel (for personal travel). Out of all the things that hotels offer on the surface, there is so much more if you dig a bit deeper. Being a classic millenial, I think that I deserve the finer things in life — and what that means is upgrades to First Class on planes, and upgrades to suites at hotels. Getting the infamous upgraded suite can be tricky, but I hope to shed some light on my experiences.

Some hotels don’t have the option to upgrade, some don’t have enough rooms, and some are just too popular to even try. But this last weekend I decided to stay in Chicago after a work event in the city, and I really thought I had a good chance at an upgrade. While I usually don’t stay at SPG properties, this year I am making a push to try more SPG brands, and I thought what better time than the present. The W Chicago-Lakeshore had some really low fares (I think due to the fact that it was end of January in Chicago), and I figured that maybe there wouldn’t be a ton of guests given the time of year. While my data points are low (I’ve never been upgraded), leading up to the stay I thought I had a good chance at an upgrade.


I read quite a bit about different strategies in securing an upgrade. It sounds like most people are split in regards to calling early, or waiting, and not pushing the subject (this comes down to people, not a computer, so ultimately they can decide just not to award you a set). I decided to wait and see if the hotel reached out to me. Even though I am Platinum Preferred with SPG (through my Marriott status), I had booked a non-refundable, member exclusive rate. In other words, I was the least profitable customer to the hotel that weekend.

While that low rate meant that the hotel may have put me last on the list for a possible upgrade, I think it also meant that they were trying to get rid of some rooms to ensure full capacity. Lowering the rates brings in more “casual” travelers who most likely do not carry any status with SPG. Based off of this, and the fact that it was end of January in Chicago, I had my chances around 50-60% at getting an upgrade.

What I did to try for an upgrade

There is no right way to try for a hotel upgrade. As I mentioned, you could have looked at the manager wrong and she decides not to give you an upgrade. All she has to say is that there are none available and you wouldn’t know any better. Ultimately, it really just comes down to luck.

After doing all my research, I decided to wait. I didn’t want to force the issue, or raise any unnecessary flags. I did expect to get some kind of correspondence from the hotel in the week leading up to my stay, in which I would have responded, but I didn’t receive anything until the day before. Some hotels will send an email a few days prior, which will prompt for any special requests, but that was definitely lacking here.

The day before I’d be checking in I gave the hotel a call. My girlfriend was going to be checking in for us as I’d still be working (this may have caused a bump in an of itself) so I needed to get her name on the reservation anyways. As part of this conversation I slipped in a question about the possibility of an upgrade. The lady initially told me that I was eligible for an upgrade to a “Lakeview” room, as we were booked in the cheapest room possible, looking at another building. In all honesty, this was perfectly fine — we didn’t really need any more room, and having a view of the lake is really spectacular. But I decided to push the subject a bit more. I asked about a suite upgrade, and then asked to talk to her manager. I was extremely polite, but consistently fed excuses. While this wasn’t what I had anticipated, I decided to concede for the day an deal with it upon arrival.

I mentioned that my girlfriend would be checking in for me. What this meant was that the platinum member wouldn’t be facing the manager asking for an upgrade. I don’t think this should matter, but I think it may have had an impact. I gave her direction on what to say, who to ask for, etc., but ultimately she was fed the same excuses that the suites were full for the weekend. There was one last option, as I was coming about 2 hours later to put my card on file and get more keys. When I arrived I asked if it was possible to get upgraded to a suite — playing ignorant as if I didn’t know this was already asked. Same thing — no suites available. I’m still not sold this is true, I just think they didn’t want to make housekeeping clean a suite when I was paying such a low rate per night. But at least they were consistent! But in the end we were given a room with a lake view — a really above average experience.


Overall, we were very pleased with our stay, and I will definitely revisit if in town.

What did I learn

As this was my first time really trying for a suite upgrade, there were definitely some major takeaways for next time.

  1. Find some way to get in contact with the hotel a few days in advance. I don’t think they will be able to give you a suite then, but at least you’ll get on their radar. I don’t think that I necessarily messed up in this sense, but who knows what would have happened if I called earlier.
  2. They are more likely to give you a suite upgrade if you have some kind of reason. Whether it be your anniversary or college reunion, always play to their emotions!
  3. To play off of that — you’re dealing with real people here, not a computer. Unlike airline upgrades that go off of a pre-defined list, hotels will give out suites only if they are available.
  4. Pray! Ultimately, this comes down to luck, so your best bet is to just hope and prey.

Tucker is an avid points and miles enthusiast. Being fully involved in the world of credit cards and frequent flying for only a few years now, he brings a very fresh and unique perspective to the world of travel.

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