What I look for when booking a hotel?

I just got done booking a weekend hotel stay in Chicago — I don’t want to say when, as I’m afraid people may begin to question my sanity, but I will say it is very soon. Long story short, I have to be there for work until late on a Friday and thought I might as well stay through the weekend. I’ve only ever been to the city once before and absolutely fell in love with it, so I’d love to take advantage of the opportunity while I’m already there.

One of the really cool things about trips like this, without any real constraints, is that I can pick virtually any hotel I want — which is my “kid in the candy shop” type situation. It also helps that no one would actually chose to come to Chicago at this time of the year.

For the purposes of this post, I wanted to talk about what exactly I look for in a hotel. What are the specific features I look for? Which features weight heavier than others?

Note: For the purposes of this post I will use this upcoming stay in Chicago as my point of reference.

Opportunity to try new hotels

First and foremost, if I can I want to stay at a hotel I have never stayed at before. As someone who considers this a hobby, being able to try new hotels is quite a thrill. Whether it is trying a hotel chain I’ve never been to, or experiencing a different brand from an already familiar group, there is some kind of thrill in the unknown.

Also, for the sake of sharing on here, it is a good idea to have knowledge of as many hotels as possible. Of course the unknown can be bad, I want to try all (or as many as possible) for my own knowledge.

Delta Resort Victoria, British Columbia
In Victoria, British Columbia I stayed in the Delta Resort, a brand owned by Marriott.

So this was on the top of my list for this stay in Chicago. If I had to choose I’d usually pick a Hyatt hotel. I find their products to be the most consistently above par, and I have always been well taken care of from a customer service point of view. But for this trip I decided that I wanted to try an SPG property. I’ve heard so many good things about SPG, and I think most would agree that it is the most comparable to Hyatt. ‘On top of that, I’ve actually only stayed in one other SPG Property (at least as far as I’ve tracked it), so I really just wanted to see more of what they have to offer.


Whenever I travel personally, I like to be as close to the action as possible, especially in large cities. While it may be a bit more expensive, I’d rather pay a bit more and not have to worry about getting an Uber every time I want to get somewhere. I find myself making some concessions on transit time/cost, in the event that a certain hotel is particularly appealing, but I would say that location is high on my list of factors.

In terms of Chicago, if you are downtown you can get anywhere. Like any large city, it is pretty easy to get from point a to b no matter where you stay. I knew that I wanted to be relatively close to the major spots, but I also was flexible where exactly that was. In other words, location didn’t bear much weight. While I didn’t take this into as much consideration, getting around will be very tricky this time of the year, so maybe I should have considered it more.

The Brand

As someone who travels often, I have quickly realized the benefits of being loyal to a brand. Hopefully with my travels I’ll be able to become an elite member and enjoy that loyalty across many brands. Ultimately my decision of a hotel weighs heavily on the type of hotel it is — for instance, before reading any reviews or looking at price, I’d prefer to stay in a Hyatt Place before a Hampton Inn. Without considering anything else, there seems to be entirely too much disparity in Hilton and Marriott products. Sure, there will be quality low-rate properties on other brands, but I know (for the most part) exactly what I’m getting with Hyatt or SPG, and that is a higher class product. I think it obviously has to do with the portfolio — Hilton and Marriott have way more hotels for you to compare.

For the Chicago trip I figured I’d do a hotel in the Marriott/SPG portfolio, as I have Platinum status with both. While I am a true believer in Hyatt, I wanted to expand my horizons with SPG, and it doesn’t hurt that I have Platinum status through Marriott. For a weekend like this, it is nice to cash in on the benefits you earned from achieving that status.

Elite Qualifying/Promo Targeting

One of the biggest things I look for when traveling on “loose” weekends is what those stays/night can accomplish. Is there a chain I am close to earning status with? Is there a promo going on that represents oversized value? While it is not a true mattress run, it should be treated as one.

Obviously, no matter where you stay, you should always be earning points or miles (or whatever you prefer). But when it comes to hotels, I look more specifically where I need to earn those points, as I know I have options. Being so early in the year now, it is hard to know where I may come up short at the end of the year, or where work may take me in the future.

For the sake of my upcoming trip I knew I didn’t want Hyatt. Travelling weekly and staying at a Hyatt, I’m not worried about achieving Globalist status with World of Hyatt this year. While this would definitely help get me there faster, I wanted to begin my journey with Marriott/SPG for the year. And what better way than an SPG property downtown Chicago. I have yet to determine my exact SPG/Marriott plan for the year, but I’d like to ideally get as many nights as possible with SPG.

There is also an SPG promotion going on, which rewards for weekends stays! This was more of an added bonus, but it definitely didn’t hurt!


I’d be lying if I left price off this list. As a smart (don’t want to say frugal) traveler, I will never pay an exorbitant amount for just a weekend away. As someone who scrutinizes every dollar spent, I need to find some sort of value in whatever I hotel I book.

Fortunately, for this Chicago trip, it is probably the slowest time of the year for tourists. Someone had mentioned it may be cold. What that means for me is some really great deals on hotels, though. I am only a few blocks away from all the major downtown attractions and right on the lake. All this for the low price of $93/night — which hopefully turns into a suite!


This comes in as a very low priority, but if it comes down to comparing two hotels, I’ll do my research and figure out which one has more to offer. Maybe there is a nice hotel bar that’ll get me some free drink coupons? Or maybe a lounge? Or maybe just a really nice gym?

These are the things that I put some value in that many others may not. It also really depends what the purpose of my trip is. If I am waking up early, going out all day and coming back late, I probably don’t care about the amenities. But if I have time, I might as well try to enjoy some of the things I am already paying for.

This Chicago trip had me doing a bit more research than I really ever have for a hotel. As stated above, I knew I wanted an SPG property. I knew the relative price range I wanted. And I knew the location … Chicago. But there were a few different options that fit all of these, and this is what led me to my deep dive.

As a recent top-level elite, I have never experienced a true suite upgrade. I’ve been upgraded to rooms with better views, or on higher floors, but I’ve never truly been upgraded to a suite. One of the things that I was looking for in my weekend away to Chicago was the possibility of getting upgraded. I knew I’d be getting a great deal on any standard room I booked, and from there it’s all up to the hotel gods to score me an upgrade!

The Seattle Space Needle lit up at night.
At the Hyatt Place-Seattle/Space Needle, I was “upgraded” to a room with a direct view of the Space Needle.

If you ever find yourself in a similar situation, the internet (a.k.a FlyerTalk) is your friend. Almost every hotel in the world has a thread dedicated to it. Talking about everything from prices, parking, what room to request, nearby eateries, and in my case, chances of an upgrade! There is no one formula to getting an upgrade, but through others experiences you will be able to determine how likely your chances are. While my initial purpose was to determine the hotel that gave me the best chance of scoring an upgrade, I was able to gain so much more valuable insight.


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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