Anyone can do this — it’s very easy

I don’t always get free upgrades on flights. It’s more like maybe only once in every 10 flights. But it’s still worth it. Sitting in business class is such a great experience if you’re on a long-haul flight. And if you get it for free, that’s a bonus.

It’s the same with hotel stays. If you can get upgraded from a standard room to a deluxe room, it makes your stay just that little bit better.

So, how do I get these upgrades?

It’s so simple that you’ll roll your eyes when I tell you. I simply ask. That’s it. If you don’t ask, you usually don’t get. If you ask, sometimes they’ll say yes. It’s just a numbers game.

There are things you can do to improve your chances of getting an upgrade though.

Upgrades at hotels

My wife and I often travel for months at a time, so often we’ll book a week or longer at a hotel. The longer you stay, the higher your chance of either an upgrade or a price reduction.

When we stayed in Phnom Penh for 6 weeks, we ended up staying in the same hotel for about 5 of those weeks. We initially booked 3 nights to see what it was like. It turned out to be perfect. So we just asked if we could get a free upgrade or a discount if we stay a couple of weeks.

It was a small hotel, so the manager and staff had already got to know us a little, which helped. She said she’d need to check with the hotel owner but was sure she could help. Later that day she offered an upgrade and a big discount if we stayed a month, so we did.

There was also a time in NYC when I had booked a 3-week stay at a hotel. I asked for an upgrade and the receptionists said it wasn’t possible because they were fully booked. She added that as I was staying so long, she’d check again in a few days to see what was available, as some guests would be leaving. Three days later I got an upgraded to a huge room with an awesome view. She said I could stay there for the rest of my stay.

It also helps to be friendly. The staff often have a tough time dealing with customers, so be nice and you can really stand out from the crowd.

Upgrades on flights

I find it’s a bit more difficult getting upgraded for flights but it does happen. I’ve found two things that help. The first is to dress like you’re a business class customer. They’re not going to upgrade you if you don’t look the part.

The second thing that helps is if you’re a member of that airline’s customer loyalty program. If anyone gets upgraded, the highest tier loyalty customers will be first in line.

My wife also got upgraded once because the video monitor at her seat wasn’t working. She asked if it could be fixed. They said it couldn’t be but that there was a free seat in business class if she wanted to sit there.

If you want an upgrade, just ask. It works. Sometimes.

This is also true for almost anything in life. Ask and you may get what you want.