Booking flights can easily become one of the most stressful parts of planning a trip. Airfare isn’t cheap, and with prices constantly changing, it’s natural to worry that if you book now, you might miss out on a better deal later.

We often think, “Maybe if I wait just a little longer, the price will drop.”

I used to do that too — spending countless hours checking different websites, second-guessing every decision, and hesitating in hopes of catching the “perfect” fare. But in reality, trying to time flight prices is like trying to time the stock market — it rarely works out. More often than not, you end up losing.

Why? Because airfare is unpredictable. The best time to book is usually now.

During a visit to Google Flights, I learned that their analysis of thousands of flights showed the average price drop from waiting is about $50 USD. Sure, you might save that amount — but you’re just as likely (if not more) to see prices jump by hundreds instead. (Sales and mistake fares not included.)

As someone who looks at flights daily, I’ve learned to stop second-guessing. If the price feels right for you, book it and move on — even if it drops later.

In this guide, I’ll show you exactly how I approach booking flights — and how you can do it confidently too.

Step 1: Check for Flight Deals

I always start by browsing deal sites like Going, Holiday Pirates, and The Flight Deal to see if there are any active fare discounts. Sometimes I get lucky and find a great offer — in which case, I book it and I’m done. But more often than not, there’s nothing that fits my plans, so I move on.

Step 2: Explore Major Routes

If no deals are available, I turn to the ITA Matrix, a powerful search tool used by travel pros. While it only includes major airlines and excludes budget carriers, its flexible calendar view lets you see prices across an entire month — helping you identify when fares are at their lowest.

Flexibility with travel dates is one of the biggest advantages when booking affordable flights. Even better? Flexibility with your destination. If you’re open to where you go, try using “Everywhere” as your destination on platforms like Skyscanner or Google Flights — you might uncover unexpected bargains.

For now, though, I’ll stick with specific destinations. Let’s take a look at an example route: New York to Barcelona.

You can quickly spot that the lowest fare on this route is $404 USD. However, once you click through to select your travel dates and view booking options, you’ll see all the details laid out clearly.

As shown, the lowest round-trip fare is $404 USD with TAP Portugal, departing from Newark and including a layover in Lisbon. However, for only $457 USD, you can book a nonstop flight with United — a far more convenient option overall (highlighted in red in the screenshot above).

After that, I head over to Skyscanner to compare prices and check if any budget airlines operate on the same route.

Here’s a look at New York to Barcelona on Skyscanner:

As you can see, Skyscanner returned similar results, including a slightly lower fare for the TAP Air option. While the price difference isn’t major, Skyscanner did display some flights that didn’t appear in the ITA Matrix search — like the direct Lufthansa flight — which shows it’s worth using multiple tools to compare options.

Step 3: Explore Regional Flight Options

Next, I use Google Flights to search for regional alternatives. For example, if my destination is Barcelona, I’ll check whether flying into a nearby major hub — like London — is cheaper. From there, I might catch a low-cost flight to my final stop.

Although this approach requires booking two separate tickets on different airlines, it can lead to significant savings. I once flew to Dublin, then took a Ryanair flight to Paris and ended up saving $200 USD compared to flying direct.

In Europe, this strategy works especially well thanks to the abundance of airports and budget carriers.

If you’re not familiar with which low-cost airlines operate where, just visit the website of your destination airport to see a list of airlines.

Or, an easier method: plug your departure airport into Google Flights and set a broader region, like “Europe,” as your destination. This gives you a map overview showing the cheapest options from New York to cities across the continent.

I notice that flying into London is slightly cheaper at $356 USD — making it one of the most affordable routes from New York to Europe. However, that price doesn’t include any baggage. Once I adjust the filters to include at least one carry-on (since most travelers will need one), the total comes to $401 USD — only a few dollars less than booking a direct flight to Barcelona on a single ticket.

At this point, I stop my search. If the price difference had been more substantial, I’d consider whether booking two separate tickets would actually be worth the savings.

It’s important to weigh the full picture — including immigration checks, switching airlines, potential delays, and how much your time is worth. Adding a layover just to save a small amount often isn’t worth the hassle.

While I’ve used this strategy before to cut costs, in this case, the savings just don’t justify the extra steps, so I move on.

Even when the price looks good, budget airlines’ extra fees can quickly erase any potential savings. They often charge for everything — checked bags, carry-ons, printing your boarding pass, paying with a credit card, and more. Always calculate the total cost (fare + fees) before deciding. Plus, with an extra stop, you might end up spending more on food or airport expenses too.

As a general rule, I only consider this method if it saves me over $150 USD and I have at least three hours between flights. Since you’re booking separate tickets, one airline won’t help if you miss the next flight due to delays — and most travel insurance won’t cover you if your layover is too short. Always build in a time buffer.

Step 4: Check Airline Websites Directly

After using those comparison tools, I also check the airlines’ own websites. Many airlines offer exclusive rates to encourage direct bookings, so it’s worth a quick look.

In this example, though, the fares on the airline websites were either the same or higher. For instance, the United flight found earlier through ITA Matrix at $457 wasn’t any cheaper on their site.

That’s not always the case, though — sometimes booking directly through the airline’s website will give you a better price. It’s worth doing a quick check just to be sure you’ve covered all your bases.

Step 5: Lock It In

Once I’ve booked my flight, I make a note to revisit the fare about 23 hours later. Since most airlines offer a 24-hour cancellation window, I’ll do a quick check to see if the price has dropped. If it has, I rebook. If not, I keep my original ticket.

After that? I move on.

Even if I see a better deal later — a sale, a random price dip — it doesn’t bother me. You can’t predict the future or know when prices will shift. You can only make the best decision with the information you have when you book.

Sure, you might find a $5 discount on some obscure website after hours of searching. Or maybe (though unlikely) your flight drops by $200 the next day. But it could also go up.

In the end, stressing over it just isn’t worth it.

If you constantly worry about getting the “perfect” price, you’ll be stuck in a cycle of hesitation — and likely end up paying more. Not to mention, your time is valuable. Personally, I’d rather spend an hour booking and get on with my day than waste hours hunting for a few dollars in savings.

This entire process — from deal hunting to final booking — takes me about 40 minutes. After that, it’s done. I don’t second-guess myself. Life’s too short to stress over airfare.

So spend 30–40 minutes finding a price you’re comfortable with, book the flight, and move on. You’ve got a trip to plan.