This was a wonderful surprise to me in the past year and I actually forgot to write about it. I guess I was just so overcome with how amazing of a deal I managed to get one day when I was flying from Florida to Mexico about 4 months ago.
Someone suggested that I get involved with certain websites such as Going or with PremiumFlights but honestly, this didn't result in a big enough discount to entice me.
The trick with this or basically anything else that looks like it is to have very flexible dates and put your information in there a LONG time before you actually want to go. I have heard that rarely is there something that is coming up in the next couple of days that is going to be heavily discounted but I suppose it could happen. I personally do not fly enough for this to happen to me much. But I did do something that lately I find myself saying more and more frequently as time goes by.

I mean, who wouldn't love to have all that legroom. I am not a giant human being, but I am larger than the size that it seems most airlines have allotted us in economy and if I have the opportunity I am willing to pay a BIT more to get a nicer seat. I'm not willing to pay 3-5 times the price for this though, and that seems to be the industry ripoff standard if you are just doing a simple search on something like Kayak or Trip.com.
The secret I was talking about before and that I find myself realizing more and more often about how one can score cheap business or even first class tickets lies in something that 30 years ago the world almost completely abandoned but is making a comeback: Travel Agents
By the recommendation of a friend I got involved with a real person, a real travel agent that I can communicate with in a messenger, not a maze of FAQ's. This woman is able to accomplish anything you want and some of those things are things that they aren't going to mention to you unless you ask.
one of those things that my friend explained to me is keeping their ears to the ground as far as a premium seat between two destinations for just some very wide range of dates in the future.
The downside of this is that you need to be prepared and capable of having flexible dates like this and you also need to be prepared to go during all of whatever those date are that you specified.
I realize that this is not going to apply to a great many people but for digital nomads who don't really have to go anywhere at any specific time it could be idea.
With my agent I just specified that I wanted to fly to Mexico City from Florida any time in the month of June. I told her this around February at the suggestion of a friend and I honestly didn't expect much to come from it.
Enough months went by that I kind of forgot that I ever asked the agent to do this for me but one day she contacted me and showed me that an economy class ticket from Miami to Mexico City was $320 but a first class ticket had come available for $380 and included priority everything as well as lounge access in Tampa.
For me, the extra $60 is totally worth it because if you are in an airport and have a sandwich and a beer it is probably going to cost you at least $30. But only now you get to go to the short line at the check in counter that makes you feel like a king, and you get to go through a special security line and also immigration line that is reserved for the rich and famous I guess.
It makes the airport experience so much better.
I wish I was reporting to you that there was some sort of magical website that posts all of this stuff but I am pretty sure that all of them that claim to do this, including the two that I listed at the start of this blog, are not really able to do that.
While I do not know exactly what sort of tools agents have at their disposal, we kind of have to assume that they are not things that just anyone has access to. I really don't care what they are doing to be honest with you, I just like that I can get some perks like this for very little additional money.

Apparently these upgrades are more prevalent and more likely to happen on domestic flights in the USA and with a shorter time frame. I don't travel domestic in the USA so that isn't something I am going to be able to test out.
I suppose the moral of the story here is that if you can, at least have a look at an agent. The internet was our savior back in the day I think, but these days I kind of feel like it over complicates things often and in an effort to always have the lowest price they can often get scammy by including seriously budget airlines into your search result mix as well.
If you travel, at least have a go at trying a travel agent. Ever since I stopped trying to book my own tickets and started using an agent I have noticed that things have gotten a lot easier for me... and I suppose there is always the chance of a luxury upgrade as well.
In all the times that I have used this particular agent, I have compared the price that she quotes me for a flight to exactly that flight on a major booking website of some sort and her price is always extremely close to what the cost would have been if I dug and dug and dug to find that flight on my own.
What is your time worth?
Never thought of using this method but then you have to be very flexible and that does not really work when you are planning ahead. I have been accumulating points to the extent I have enough to upgrade or even get free tickets for international flights so I am looking forward to when that happens next flight. The walking around late at night when everyone has gone to bed also works as long as there is empty seats in business class.