How to Use Points and Charm to Score an Upgrade ( The Dossier, Portland OR)

One secret to travel hacking is making sacrifices in the name of saving money. Occasionally, when booking hotels for points on the Chase Ultimate reward site you can get a nice discount if you book non-refundable.

Now I know there are a lot of “what ifs out there. I’d like to think if you had a truly epic emergency you may be able to work something out with Chase or the hotel, but thankfully 9 out of 10 times this wont be an issue.

I was struggling when looking for affordable hotel options in downtown Portland, Oregon. I was booking for my birthday weekend, a Friday-Monday in August. Most rooms in cash value were a minimum of $250 dollars a night. I don’t have unlimited points, hence what to do?

Originally, I was thinking about using 12,000 hyatt points a night( converted 1:1 from ultimate rewards) to book the Hyatt in downtown Portland. The problem was that they only had reward space for 2 of my 3 nights, and moving around wasn’t a viable option.

I then stumbled onto the Westin Portland. They had a non-refundable rate for the 3 nights at $200 a night or 13,000 ultimate reward points (1.5 cents per dollar). I figured why not. The reviews were good and I have Starwood gold status which helps give me upgrades.

I booked the hotel, and didn’t think much about it. Until I got an email a few weeks before the trip stating The Westin Portland was changing hotel brands!

At first I was thinking, “This is BS! Who is the Dossier?”.  Also I have no status with them, so i won’t get any perks. But I reconsidered.

They asked me what could they do to make my stay special. I replied that its my birthday weekend and would love some good food recommendations, as well as any possible room upgrades. I didn’t hear back.

At check-in I was impressed with the lobby and check-in area, the hotel didn’t seem super corporate and had a nice boutique feel. The check-in guy first told me I had three rooms (which I found odd) then said sorry its just one. I joked, “give me the best one of the three. He replied, “no problem your going to get the premium corner room with the view of the city. Sweet!

A nice view of downtown Portland from my window.

After arriving to the room, and doing a quick sweep I noticed on the desk a note and little present.

I thought that was an awesome gesture, they even included a white chocolate cereal bar.

On top of that, they left me a Portland magazine with post-it suggestions for food options. Personal touches go a long way for me.

The morale of the story is: Take risks in your bookings for maximum value and politely ask for things to make your stay more special. You never know what cool extras may come your way.

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