Having visited 44 countries, I’ve become skilled at booking flights. Many would agree that I have perfected the art of finding cheap flights. For years, I’ve relied on intuition and trial and error to determine the best time to book. In recent years, data has become more accurate, leading to more effective tools that help us secure better flight deals. I like to use a combination of smart data, such as Google Flights and ChatGPT, along with tools I’ve used for years, like Skyscanner. And, of course, I still trust my gut when it comes to booking. In this blog, I’ll share my top tips and best practices on how to find cheap flights.
1. Flight Booking Myths to Find the Cheapest Flights
There are some common myths about booking flights that you should know. Two big ones that can save you time and energy.
- The first is that you should search for flights in incognito mode. The myth behind this is that flight apps track your cookies, and because of that, they won’t show you the best deals since they know you’re looking to buy. I have tested this tactic many times and haven’t noticed any price difference; therefore, I recommend avoiding the hassle. Some people also clear their cache and browsing history every time they search. There’s no evidence to suggest that flight booking apps are that advanced.
- The second myth is that booking on a Tuesday is when you are most likely to find the best deals. This might be true, but according to Google Flights data, the actual savings are only about 1.2% on average if you’re lucky. And this is the difference between Tuesday, the cheapest day, and Sunday, the most expensive day to book. Overall, the day you book a flight has a minimal impact on the price.
2. The Best Booking Window to Find Cheap Flights When Traveling Abroad
Based on years of my own flight booking data, I have developed my own best practices for booking flights. This applies to domestic flights, as well as travel within North America and overseas. Below, I will break this down.
Domestic Flight Booking Window for the Cheapest Flights
My recommended booking window for domestic flights is 30 to 45 days before departure. Usually, if I see a price I like at 45 days, I will book that flight. It’s up to you to research the destination and determine what a good price looks like. I will discuss some tools shortly to assist with this process.
Finding Flight Deals to North American Destinations
If I am flying within North America but outside of Canada, my rule is 60 days. So, anywhere in the US or Mexico, this is generally my guideline for finding the best price. If you are a risk-taker, you could hold on until about 50 days, but I wouldn’t wait any longer than that, as prices are likely to start rising.
How I Find Cheap Flights Overseas
This is my sweet spot, where flight booking skills can save you hundreds or even thousands. When I say ‘overseas,’ I mean Europe, Southeast Asia, India, and Africa. I have a target price in my head for each destination from Toronto. For example, Europe costs around $700, while Southeast Asia and India are about $1,000 CAD.
If you are headed to Southeast Asia or India, you should find the best price around 4 months before departure. For Europe and Egypt, booking two to three months in advance. Of course, these aren’t strict rules, but they’ve worked well for me over the years.
These best practices have helped me, and they will help you; thankfully, we now have access to reliable smart data. So, let’s dig into that.
3. How to Find Cheap Flights Using ChatGPT
ChatGPT is a game-changer, and this also applies to booking flights. I use ChatGPT to confirm my thoughts about booking a flight path. I ask it for advice on when to book my flight and what a great deal looks like. There is plenty of flight booking data available for ChatGPT to draw from, making the process easier than ever before. ChatGPT will offer a detailed overview of your selected flight path.
I am currently planning a trip to India, and these are the questions I asked ChatGPT.
When is the best time to book a flight from Toronto to India to get the best deal?
What would a great deal look like?
The response I got to these questions was that I should expect my best deal starting four months before departure. However, the best deal might be available as late as 49 days before. I was warned that waiting until 49 days out could be risky, and I might want to book earlier. It told me that $700-900 is a super deal and to grab it if I see it. If I pay $900-1200, that’s a bookable deal.
I am currently using the ChatGPT information to help me book this flight to India.
4. Spend Some Time Researching Google Flights Data
Google Flights is a helpful resource, providing valuable tips on how to find cheap flights. They have recently released new data on the best times to find affordable flights abroad. With millions of users relying on Google Flights as a travel resource, they have access to a wealth of valuable data.
Below are some of Google Flights’ key findings that I found helpful. These are the days before departure when you’ll find the best prices according to Google Flights.
- If you’re heading home for Christmas, 51 days before departure.
- For domestic travel, 39 days.
- For Europe, 48 days.
- International 49 days or more.
- Mexico/Caribbean 44 days.
And these are just a few of the highlights; there is much more valuable data from Google Flights that will help you find cheap flights.
Sign up for the Globe Digger Newsletter
5. Set Price Alerts with Skycanner
You now have some of the basics on how to find cheap flights. It’s time to put them into practice and start tracking popular flight routes. I recommend finding a flight booking app and setting price alerts. I use Skyscanner because I believe it’s the only app you need, as it compares all booking sites to find the best price. Get into the habit of checking back regularly and setting new price alerts, since new flight paths are added almost daily. When prices change, you will receive an email from Skyscanner.
I’m sharing an image with my affiliate link below so you can set your own price alerts. By clicking the link, I may receive a small commission.

6. Look for an Early to Mid-Week Departure
You can save even more by departing mid-week, Monday to Wednesday. Google Flights data indicate that you could save up to 13% by flying mid-week instead of on a weekend. I prefer to depart on a Monday or Tuesday, as these days tend to be the cheapest and the airports are less crowded.
7. Book Flights With Layovers
When I travel, I love booking flights with layovers. This can mean spending 24 hours in a new country or just a few hours at a connecting airport. Regardless, I enjoy the airport and flight experience. If you book flights with a layover, you can save 22% compared to flying direct. This data is from Google Flights. You can save money on your flight while enjoying the journey.

8. Be Flexible on The City You Fly In to
When I fly to a new country, I set my price alerts for multiple cities. If you’re planning to explore a new country, choose several potential airports to fly into. Some people even look at nearby countries and cross the border by land if they find a great deal. For my upcoming trip to India, I’m looking at flights to New Delhi and Mumbai. So far, flights to Mumbai are roughly $300 cheaper on average. Being flexible with your destination can make a big difference in the price of your flight.


My Flight searches to Mumbai and New Delhi for my upcoming trip to India. You can see the flights are $350 – $600 less to Mumbai than to India.
9. How to Find Cheap Flights from Airlines
I always check directly with the airline carriers to see if I can find a better deal, especially when flying domestically. Even if the same deal is available through the booking apps, I still prefer to book directly with the airline. The main reasons are that it’s easier to change flights and you receive customer service from the airline. When you book through travel sites, this isn’t always the case. Often, with an app like Skyscanner, there’s an option to choose the airline to book through. Avianca, when travelling in South America, is one airline that I select through the Skyscanner app.
10. Use Travel Points Credit Cards to Book Flights and Other Travel Services
This flight booking hack may not directly help you find cheap flights, but it can help you save on your flight. If you haven’t already, consider getting at least one travel points credit card. I personally have three: Scotiabank Passport Visa Infinite, RBC Avion, and BMO World Elite. By using these cards, you can earn points that can be redeemed for travel services, including flights, car rentals, hotels, tours, and other travel-related expenses.
My personal method for using points cards is to apply my points after purchasing a flight. It’s relatively easy to earn between $150 and $300 in points. I then apply these points after I book a flight on Skyscanner. A $300 discount on an $800 flight can make a significant difference. Of course, you can book flights directly through the credit card partners, but based on my experience, you tend to pay more that way.
If you apply these flight booking tips, you’ll start finding better flight deals. These best practices have worked well for me over the years. I hope this blog helps in your search for how to find cheap flights, just as it has for me. Good luck and happy travels.
For more travel tips check out the Travel Tips section of my website.
To learn about more travel brands I trust, visit the Travel Resources section of my website. These links are affiliate links through which I may receive a small commission if you click on the link or make a purchase.
If you’re interested in finding out more about how I plan my travel, check out my blog, My long-term Solo Travel Planning Methodology
Check out all of my blogs in one place here.
Subscribe to my YouTube channel
Follow me on Instagram
Listen to my Solo Travel Podcast on Spotify.


Leave a Reply