Lileks: What's best time to make an airline reservation?

The upcoming holidays means travel for many. In the old days, you called a travel agent, and a week later a ticket arrived in the mail. It was very precious and could not be replaced, and you felt as if you'd been entrusted with a Dead Sea Scroll.

Now you do it yourself, and it's no fun. You get excited when you see a reasonable fare, and then you remember that you also have to pay for a seat. The ticket price just gets you through the door. The moment airlines realized they could charge extra for seats must have been a startling revelation: "Why didn't we think of this before?" Then they lit piles of money and danced naked around a statue of Mammon.

Anyway. The last time I went online to make a reservation, the airlines page had a message for me: "You've searched for flights from MSP to PHX twice before. Would you like to continue?"

I panicked and closed the browser. They were on to me. Close the blinds! Douse the lights! Ssshhh! They'll hear us!

This sounds a bit unhinged, I know. But we have come to believe many things about the airline reservation sites — how they track you, what's the best time to book and so on. There's an art to it. Only a fool blunders in and punches in dates and destinations. You have to approach this with the stealth of an assassin, and I'd blown it all somehow. They knew what I wanted.

Well, I was not without my own skills. Let's try this again. First, clear the cookies. Empty the cache. Restart the computer. While it's rebooting, change clothes. Apply a false mustache. Sell the house, move. Tape two fingers together so your typing will have a different rhythm.

Let's try this again. Fire up the VPN! This is a program you run that fools them into thinking you're coming from somewhere else, like the Netherlands or Antarctica. Just to be extra crafty, I used a VPN to get to my VPN, which is like going to a dress-up party with one costume over another. Everyone thinks you're a skeleton, but you're really a vampire.

"Hello, Dracula, where would you like to go?"

Damn. They saw right through that. OK. Empty cookies, dump the cache, reboot, wipe off the mustache and try again.

No, that's what they want. They're expecting me to try again, and when they learn that I want to go on an airplane, they'll bump up the fares. That's how it works, you know. Then I realized that I was making this reservation at 2 p.m., which is the worst time because there are countless other would-be travelers doing the same thing.

The other worst time is 2 a.m., because they assume you can't sleep because you've been confronting the rote habitual nature of your life and have decided to do something, anything, to break out from this stultifying routine, so you browse airline sites on your phone in the dark, hoping your partner doesn't wake and ask what's wrong, because then it would all come out. "If I don't go to British Columbia I shall die."

I'm sure there's a website with an exhaustive list of the times you should not book a flight, as well as the days. I'm sure you shouldn't do it on a Tuesday, unless you visit the site in incognito mode, wear a bag over your head and type your requests using chopsticks. Wednesdays also are bad, but not as bad as Thursdays, when all fares go up 945% for seven minutes, just to see who bites.

For all my evasions, I still suspected the site knew me and would punish me for my long patronage of their airline: "We got this guy right where we want him: satisfied return customer. Give 'em the business."

But I had one trick left: I searched for flight and hotel. I'd never done that before, because I never need a hotel. But they don't know that. "Can't be him; must be a new customer. Lower the fares. This time."