airplane seat and window

5 Simple Tips for Booking a Flight the Right Way

There are so many tips for booking a flight available online!

And, when you begin to research which are the best places to search or what day of the week you’ll find the best deals, it inevitably leads to head-spinning analysis paralysis.

This guide will show how to book a flight the right way. And, even though tips about how to book a flight online come and go, the tips below are what I’ve used successfully over and over.

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5 Simple Tips for Booking a Flight the Right Way

1. Book in an Incognito Window.

I disagree with anyone claiming that searching for flights in a private browser window doesn’t help save money. I’ve seen firsthand for several of my own flight searches done in regular browser windows how prices went up after repeated searches. Yet when moving to a different device in a private browser window, the original and lower price reappeared.

You’ve surely noticed the ads displayed on the websites you browse showing the exact items and services you’d been recently searching. Websites are required to inform you of their “cookie tracking.” Assuming you don’t opt-out, these cookies keep track of your internet searches and what types of purchases you’re considering.

Searching for airfare is no different. Research proves the more times you return to a website or repeat a search, the more likely you are to buy that item or service.

So, when searching for flights, always search in an incognito or private window.

In Google Chrome, click on the 3 small dots in the top right corner and choose “New Incognito Window.”  In Safari, open a browser window and select “Private” in the bottom left corner of the screen.

For the most part, you’ll avoid tracking cookies and your browser won’t store the history of the websites you visited. It isn’t foolproof but it allows you to research without worrying you’ll see the price go up before your eyes.

Computer desk

2. Use the Best Flight Search Engines.

Not all flight search engines are equal. It does matter where you search.

OTAs or online travel agencies that sell flights have an interest to show you flights that are beneficial to them. So, what’s shown as the “best price” isn’t always the case. What makes things even trickier is many of these websites are owned by the same parent company. When you think you’re comparison shopping, you might just be on a website with a different name but owned by the same company.

This reinforces the belief you’ve found the best price because they’ll all fall within the same range.

Instead, research on the best websites for cheap flights. Sites like Google Flights, Momondo, and Skyscanner are flight aggregators that pull in cheap flight data from a wider range of sites. For the most part, they don’t sell the flights directly. Once you’ve found the flight you want to book, these sites send you to book with that website or airline directly.

Momondo searches for the best price and then sends you to that site to book directly.

3. Be Flexible.

This may seem like not much of a tip, but it is! In fact, out of all the tips on this list, it’s the one that just might save the most money and help you find the best deals.

To clarify, be flexible with everything you possibly can, dates, times, destinations, airports, and routes.

If you’re committed to only flying on a specific day to and from specific places with no room for adjustments, you’ll likely pay for this convenience. 

However, small changes to your searches by a couple of days or considering nearby airports and destinations can amount to dramatically different prices. This is especially true for well-connected areas of the globe like Europe.

For example, flights to Paris may be pricier than flights to Brussels. Yet the 2 cities are less than a 2-hour train ride apart. It may make more sense to fly to Brussels and add an extra city to your trip rather than pay more to see just one city. 

If you have flexibility with your time off, why not search for the cheapest dates to fly to and from your destination and then request your days off accordingly?

airplane seat and window
Dreaming of a tropical island? Maybe the island next door has cheaper flights.

4. Do Your Research and Know When to Book.

It seems like every travel expert will tell you a different best day and time to book a flight. When, in reality, there isn’t a better day of the week to book your flight. Better prices and good deals can come along at any time.

But, you can improve your chances of knowing about cheap flights and even booking a mistake fare. The easiest way to do this is to sign up for an airfare alert service like Matt’s Flights or Scott’s Cheap Flights. Once you set your home airport, these services send email alerts with the latest best flight deals.

You can also do your own research. Websites like Google Flights, Momondo, Skyscanner, and the Hopper app allow you to search calendar views to see prices across a range of dates and identify the cheapest days to fly. You can also use explore features that let you see prices from your home airport to a range of destinations in a country or region.

No matter how you do your research, act decisively. I’ve learned this lesson the hard way! One of the things I love about the Hopper app is how it uses millions of data points to tell you if you should book or if you should wait. Google Flights and others allow you to set flight alerts, too, so you know if there’s been a price drop in a flight you’d been eyeing.

If you see a good deal, grab it! Remember, you’re entitled to make a change or ask for a refund within 24 hours according to Federal law, as long as you booked your flight more than 7 days from your departure date.

Hopper Color Calendar
Hopper shows a color-coded calendar to share pricing on any given day.

5. Get Creative with your Flight Bookings.

Traditional round trip itineraries aren’t always the most value for your money. Sometimes, it makes more sense to book one-ways, an open-jaw itinerary, or even add a stopover.

An open-jaw flight is when you fly into one city and out of a different city. This can end up saving you money, time, and stress.

Think about a typical European trip which usually includes a few different cities in several countries. Perhaps you want to visit PragueVienna, and Budapest. It’s better to fly into Prague or Budapest and fly out of the other.

The train can get you from city to city. And instead of backtracking to your arrival city and waste valuable vacation time, you’ll save money on transportation and likely not pay much more than you would for a typical round trip. Use the multi-city function search on most airline and travel websites to search for open-jaw itineraries.

Some airlines even allow you to add a stopover for no extra money for a couple of days in a city before moving on to your final destination. TAP Air Portugal, for example, lets you stop for 1-5 nights in Lisbon or Porto for free, before flying you to another European city.

I may not have been the best math student 😉 but 2 destinations for the price of 1 sounds good to me!

Aircraft at sunset

No matter where you want to go, knowing these basic flight search tips can help you be strategic and save money on your airfare bookings.

What’s your top tip for booking flights? 

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16 thoughts on “5 Simple Tips for Booking a Flight the Right Way”

  1. Good tips! Something that I live by too, heh! One thing that I envy is that by American law, you’re entitled to make a change or ask for a refund within 24 hours of making a booking – which allows you to book first and think later, at least for within a day, when you find a great not-to-be-missed airfare. How I wish we have that same law too here in Malaysia!

    1. Jackie Sills-Dellegrazie

      Thanks! That 24-hour law is such a perk, but also a lifesaver, too! Like when you book the wrong date (eesh!) you can fix it!

  2. Great tips Jackie. I especially love the idea of the incognito window. I’ve read this before but I never do it. It’s a good reminder for me to start using it. I also agree that flexibility in both dates and methods are key.

    1. Jackie Sills-Dellegrazie

      Incognito windows are a must, Kerri, and even then you still might need to switch devices to make sure you book at the original low price.

  3. I’m finding that Flights.Google.Com is also becoming a great search option. I prefer it to the “classic” search engines of Kayak, etc

    1. Jackie Sills-Dellegrazie

      I love Google Flights, Momondo, and Skyscanner, LeAnna. Momondo and Skyscanner are aggregators with no affiliation to big companies like Expedia or Priceline, which hopefully means I’m really seeing objective results.

  4. Great tips! Flexibility is key. I almost always end up paying more when I’m locked in to certain travel dates. It’s so frustrating. I swear by and, It’s not a sure thing, but I’ve scored some AMAZING deals with them.

    1. Jackie Sills-Dellegrazie

      Yes and Yes to Secret Flying and the Flight Deal, Mags! Both of those sites beg flexibility because when you see a great deal you have to grab it!

    1. Jackie Sills-Dellegrazie

      Momondo is really useful, Danielle, and not (yet!) purchased by a bigger corporate entity. I hope it stays that way!

  5. I use the open jaw tip a lot. I also sometimes find better prices by building the stopover into the search myself – so like if a flight from Stockholm to Seattle stops in Frankfurt – putting all of those legs into the search sometimes yields a cheaper price. Not sure why, but it does work.

    1. Jackie Sills-Dellegrazie

      So true, Laura. I think it seems illogical (Why would an extra stop be less?), which is why travelers think they have to do the round trip.

    1. Jackie Sills-Dellegrazie

      I love that! Have your dates but let the price pick the destination. A true traveler move! 😉

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