So, you’re trying to snag a flight with a layover using those fancy comparison tools, eh? Sounds straightforward, right? You just pop in your details and boom, magic. Well, let me tell you, it’s a bit more of an art than a science, at least from my countless hours spent hunting for deals and convenient stops.

My Usual Starting Point
First off, I don’t just stick to one tool. Nope. I’m usually that person with about three or four tabs open. Google Flights is my go-to for a quick overview, then I’ll often have Skyscanner and maybe Kayak running in parallel. It’s like getting a second, and third, opinion. You’d be surprised how different the results can sometimes be, or what one tool picks up that another misses entirely, especially with layover options.
I start super broad. Just my departure city, arrival city, and some rough dates. I don’t mess with too many filters at this stage. I just want to see what the digital universe throws at me. Sometimes, you see, the tools will suggest layovers you hadn’t even thought of, and that can be a good thing, or a hilariously bad one.
Digging for Those Layovers
Okay, so once I’ve got that first wave of results, then I start to get a bit more specific. This is where finding intentional layovers comes in. If I actually want a layover, say to break up a long haul or sneak in a quick city visit, I look for the filter options. Most tools have a ‘stops’ filter – ‘1 stop’, ‘2+ stops’, or ‘any’. I’ll usually click ‘1 stop’ if I’m aiming for a simple layover.
But here’s a thing I learned: just because it has a layover doesn’t mean it’s a good layover. I once saw a flight with a 45-minute layover in a massive international airport. Yeah, no thanks. I’m not trying to star in my own airport dash movie. So, I then start looking at the details:
- Layover duration: Is it too short? Is it an agonizing 10 hours overnight in an airport with no good chairs?
- Layover airport: Am I landing and departing from the same airport? Trust me, you want to check this. A layover that involves a cross-city dash to another airport is a special kind of travel stress.
- Time of day: A layover landing at 2 AM and departing at 6 AM is technically a layover, but it’s pretty miserable.
I remember one time I was flying to Asia and specifically wanted a longish layover in a Middle Eastern hub to catch up with a friend. Some tools made this easy to spot if I sorted by duration or played around with arrival/departure times for the segments. Others, not so much. I had to manually click through a bunch of options. It felt like panning for gold.

My Step-by-Step (Sort Of)
So, my actual process, after the initial broad search, looks something like this:
1. Filter by number of stops. Usually ‘1 stop’ is my target if I’m looking for a manageable layover.
2. Scan the layover cities. The tools will show you where the stop is. Sometimes you get choices, other times the route dictates it.
3. Drill down into flight details. This is crucial. I click on the promising options to see the exact layover times and airports. I’m looking for that sweet spot – not too short, not ridiculously long (unless I plan to leave the airport).
4. Compare across tools. What looks good on one site, I’ll quickly check on another. Sometimes the pricing is slightly different, or one might show a slightly better timing for a similar route.

5. If I want a really specific layover, like a 24-hour stop, I might even switch to a ‘multi-city’ search. This is more work, but it gives you precise control. For example, London to Dubai, then Dubai to Bangkok a day later. Comparison tools can handle this, but it’s a different beast than just finding a standard connecting flight.
It’s not always a perfect system. Sometimes the “cheapest” option has a terrible layover, and the slightly more expensive one is a dream. The tools are great for showing you what’s possible, but you still need to use your brain and your preferences to pick the right one. I’ve learned to be patient and to click around a lot. You’re not just buying a flight; you’re kind of curating a mini-journey, even if it’s just a few hours in another airport. And honestly, sometimes those unexpected layovers have led to cool, brief explorations. Other times, well, I just got really familiar with a departure lounge. That’s the gamble!