The ‘Anywhere’ search button is a drug. Most people approach travel like they’re ordering at a restaurant—they look at the menu, pick exactly what they want, and then complain about the price. That’s a loser’s game. If you actually want to travel for the price of a decent steak dinner, you have to stop caring where you’re going. You have to let the algorithm decide your fate. It’s chaotic, sure, but it’s the only way to beat the airlines at their own predatory game.

I’ve spent the last six years obsessed with this. I don’t work in travel. I work in a boring office where people talk about ‘synergy’ and I spend my lunch breaks staring at flight maps. I’ve realized that the ‘Tuesday at 3 AM’ booking rule is a total myth. I actually tracked 42 different routes over a 14-week period back in 2022—mostly out of boredom—and the price fluctuations had zero correlation with the day of the week. It’s all just load factors and cookies. Mostly load factors.

The time I felt like a total idiot in Milan

Let me tell you about my biggest failure because people love to pretend they’re experts who never mess up. In 2019, I saw a flight from London to Milan for £9. Nine pounds! I bought it instantly. I felt like a god. I didn’t check which airport it was. It was Milan Malpensa, which is basically in another zip code. My flight landed at 11:45 PM. The last cheap bus was gone. I had to take a taxi that cost me €110. Then the only hotel near the station that didn’t look like a crime scene was another €140. I spent nearly $300 to ‘save’ money on a $12 flight. I sat on the edge of that stiff hotel bed eating a bag of room-temperature vending machine pretzels and realized I’m not as smart as I think I am.

The lesson: A cheap flight to ‘Anywhere’ is only cheap if the ground costs don’t kill you.

Anyway, I once spent three hours researching the history of airport sandwiches because I was annoyed at a $15 ham and cheese in O’Hare, but that’s a story for another time. The point is, you have to look at the total cost of the 24-hour window around the flight, not just the ticket.

Google Flights is the only tool that matters (and Skyscanner is annoying)

I know people swear by Skyscanner or Hopper. They’re fine, I guess. But Skyscanner’s interface feels like it was designed by someone who hates eyes. It’s cluttered and the ‘deals’ often disappear the second you click them. What I mean is—actually, let me put it differently. Google Flights is the only one that feels honest. You put in your home airport, leave the destination blank, and just look at the map. It’s like a slot machine where you actually have a chance of winning.

• Set the duration to ‘1 week’ or ‘Weekend’ rather than specific dates.
• Filter by ‘Non-stop’ only if you value your sanity.
• Ignore the ‘Carbon Emissions’ stat; we all know you’re taking the flight anyway.
• Check the ‘Separate Tickets’ option but be prepared for a panic attack if the first leg is delayed.

I might be wrong about this, but I genuinely believe that if you can’t find a flight for under $400 to a different continent, you’re just being too picky about the month. I’ve seen NYC to Lisbon for $280 in November. Is it rainy? Yeah. Is it cheap? Extremely. Buy a jacket.

My extremely biased take on budget airlines

I refuse to fly Spirit or Frontier. I don’t care if the flight is $1. I actively tell my friends to avoid them like the plague. It’s not just the legroom—I’m not that tall, I can handle a cramped seat. It’s the vibe. It’s the feeling that the airline actively hates you and is waiting for you to make one mistake with your bag size so they can pounce like a debt collector. I’d rather pay an extra $80 to fly an airline that treats me like a human being instead of a piece of self-loading cargo. People who defend ultra-low-cost carriers as ‘disruptors’ are usually the same people who think cold brew is a personality trait. They’re just bad. That’s it. That’s the whole take.

The ‘Anywhere’ mindset

Last year, I ended up in Poznań, Poland. I didn’t even know how to pronounce it when I booked it. It was $19 from London (back when I was living there for a bit). I spent three days eating pierogi that cost less than a Starbucks latte and walking around a square that looked like a Wes Anderson movie set. If I had searched for ‘Cheap flights to Paris,’ I would have spent $200 on the flight and $400 on a closet-sized room. By choosing ‘Anywhere,’ I had a better experience for a quarter of the price.

It requires a certain level of comfort with uncertainty. You have to be okay with the fact that your vacation might be in a city you can’t find on a map. But honestly? Most ‘bucket list’ destinations are overrated and crowded. Give me a random secondary city in Central Europe or a coastal town in Albania any day. The coffee is better and nobody is trying to sell you a plastic Eiffel Tower.

I don’t know why we’re so obsessed with specific destinations. Maybe it’s Instagram. Maybe we just like the feeling of control. But there is a very specific kind of peace that comes from letting a pricing algorithm decide where you’re going to spend your PTO. It takes the pressure off. If the trip sucks, it wasn’t your fault—it was the flight’s fault. But usually, it doesn’t suck.

Do you actually want to go to Bali, or do you just want to be somewhere where your phone doesn’t ring? Just hit the button.