You are currently viewing How to find the cheapest dates for plane tickets to a specific destination

Traveling for less is very simple: you just have to be flexible about everything. That concept is very simple. To find cheaper plane tickets, when it’s not possible to be flexible on the destination, be flexible on the dates at least… even only 1 or 2 days before or after your desired date. It can save you literally hundreds of dollars so easily.

The best way to find a really cheap flight (paying with cash, not points) is obviously to take advantage of the 50%-off deals that Flytrippers spots on its site every day. There are dozens of them every day, but they’re obviously limited.

If you don’t find a deal, here’s how to at least find the cheapest dates with 2 very important basic caveats and the whole step-by-step process.


How to find the cheapest dates

It’s really very easy, like pretty much everything else related to travel. You just need to know how. Flytrippers will help!

The tip for everything! For literally everything touching travel, you simply need to know the tips AND take the time to apply them to compare options. It's as simple as that! There are 100+ tips in our free ebook.


Here are the simple steps (step-by-step screenshots are below):

  • Go to Kiwi
  • Input your departure airport
  • Input your destination
  • Choose a departure date range
  • Choose one of the 2 options for the return
    • Choose a return date range
    • Choose a length of stay
  • Click on “Search”
  • Sort by “Cheapest”

For more advanced searches, such as finding the cheapest dates for a specific destination, Flytrippers recommends the Kiwi tool.


Not to book!!! To search. If you are ready to book, that’s a completely separate step. Here we’re talking about the basics, knowing how to search.


2 basic caveats about the tip to find the cheapest dates

Here are 2 important basics to know:

  • It won’t be the lowest price for that particular flight
  • It won’t even be the lowest price at that particular time


Not the lowest price for that particular flight

No, the price you’ll find with Kiwi (or any other site) won’t be the lowest you can find for that particular flight.

It just finds you the cheapest dates at the precise time of your search!

And plane ticket prices change literally every day. That’s part of the basics you need to know about flights.

The chances that the cheapest price for your destination happens to be available precisely on the day you do your search… are very slim. There are 365 days in the year, after all!

That’s why the basics of finding cheaper aplane tickets is so simple: search often! Search early and often. Take the time.

So I want to reiterate that the prices obviously won’t be as good as if you look regularly and often at the deals — or if you look regularly and often at the prices manually on Kiwi by yourself of course.

Read the 31 tips on how to find cheaper plane tickets to understand the basics.


Not even the lowest price at that particular time

No, the price you’ll find with Kiwi (or any other site) won’t even be the lowest you can find at that precise moment!

It just finds you the prices for the simple combination you provide. There are so many money-saving booking tips out there, and these tricks require you to search a little differently.

For example, if you want to go from Toronto to Croatia, you’ll just see the $1400 flights if you search from Toronto to Croatia. If you’re savvy, you’re instead going to look at the cheapest flights from Toronto to Europe (often in the $600s roundtrip). And then from there to Croatia, it’s often going to be $200 roundtrip, for a total of $800.

So $1400, even if it’s the cheapest price when you’re searching from Toronto to Croatia, is really not as good as what you can find with pro tips.

But you’ve got to know how and you’ve got to take the time. That one is the self-transfer tip, but there are several others.

Read the 31 tips on how to find cheaper plane tickets and simply try them out one by one. You’ll very often be able to find cheaper than what Kiwi or any other site will spit out from the simple searches the vast majority of people always do.


Example of a plane ticket search (step by step)

Here’s how to concretely find the cheapest dates.


Go to Kiwi

Click on our Kiwi link.

Important! Click directly on our Kiwi link (and any of our links) or save our Kiwi link in your bookmarks, instead of going directly to their site! It allows you to support Flytrippers at absolutely no cost to you!


Their site looks like literally every plane ticket search tool you’ve ever used in your life. 

Kiwi’s search tool (image credit: Kiwi)


But it does have more advanced features!


Input your departure airport

Input your departure airport. I’ll use Montreal (YUL) for my example.

Departure airport (image credit: Kiwi)


Don’t forget that sometimes it’s financially worth it to fly out of an alternative airport, especially when you’re traveling with several companions. By 2025, Montreal will even have a secondary airport in Longueuil (YHU), closer than Plattsburgh (PBG). Many Canadian cities have secondary airports, including across the U.S. border.

Kiwi has a simple option for adding airports within a 250-kilometer radius.

Radius (image credit: Kiwi)


Input your destination

Input your destination. I’ll use Miami (MIA) as an example.

Destination (image credit: Kiwi)


It’s the same principle here, having more flexibility about the airport will necessarily give you more chances to find a cheap flight. And I’m not even talking about the self-transfer tip, which is a completely separate thing (and often works for longer flights).

In this case, Fort Lauderdale’s airport (FLL) is connected directly to Miami by a train, which costs US$4, so it’s worth at least comparing.

Destination radius (image credit: Kiwi)


Choose a range of departure dates

You can choose just one departure date. But obviously, the longer the range of dates you choose, the more affordable it’s going to be.

Putting in just 1 day before and 1 day after TRIPLES your chances of saving money. The price can be hundreds of dollars less, even with just 1 day’s difference.

Minimum range (image credit: Kiwi)


If you really want to find the cheapest departure date, enter the whole month (or even several months).

Even cheaper range (image credit: Kiwi)


Choose one of the 2 options for return dates

For the return date, you have 2 options.

The first is to do the same thing as you did for departure: a range of dates.

Range of return dates (image credit: Kiwi)


But also, you can choose a desired length of stay. So, for example, you can indicate that you want to leave between 7 and 10 days.

Length of stay (image credit: Kiwi)


Click on “Search”

Click to launch the search.

Search button (image credit: Kiwi)


Sort by “Cheapest”

As we just mentioned in the tips to search for Marriott hotels with points, sorting by price is always the basics for any search for anything in the world of travel.

Sort button (image credit: Kiwi)


It shows you the cheapest dates!

Cheapest dates (image credit: Kiwi)


Book your ticket

Once you’ve decided to book, it’s another thing entirely. We’ll be doing a separate post on that soon.

Just to be clear, let’s hope you don’t book the first time you do a search. Because that means you’ve almost certainly overpaid.

Search and compare often, it’s really that simple.

In short, we recommend Kiwi for research, not for booking! These are 2 completely separate steps that so many people mix up, unfortunately.

BEWARE! It's THE simple thing that many people don't know: the SEARCHING and BOOKING steps are completely separate. Never search on an airline site and never book a flight on Kiwi or with any other third-party (including travel agents) — except on the rare occasions when third-parties have a much lower price!


While you wait for the post on booking, here are the essentials as a teaser:

  • Do the same search on a few other sites to compare
  • Decide on the best option
    • Compares prices
    • Weigh the pros and cons
  • Book on the right site according to this order of priority
    • Reward program website
    • Airline website
    • Partner airline website
    • Third-party website
  • Pay with the right credit card
    • For great free insurance
    • To unlock a big welcome bonus
    • To avoid FX fees (if not in C$)
    • To earn more rewards

I’ll stop here, because that important in-depth post is coming soon, and most people want shorter posts!


Learning how to travel for less

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It’s easy to find the cheapest dates for your plane tickets to a specific destination with the Kiwi tool. You can enter a date range and directly see the dates that are the cheapest (the cheapest at that specific moment in time)!


What would you like to know about finding the cheapest dates for plane tickets? Tell us in the comments below.


See the flight deals we spot: Cheap flights

Discover free travel with rewards: Travel rewards

Explore awesome destinations: Travel inspiration

Learn pro tricks: Travel tips


Featured image: Croatian coast (photo credit: Unsplash+)

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Andrew D'Amours

Andrew is the co-founder of Flytrippers. He is passionate about traveling the world but also, as a former management consultant, about the travel industry itself. He shares his experiences to help you save money on travel. As a very cost-conscious traveler, he loves finding deals and getting free travel thanks to travel rewards points... to help him visit every country in the world (current count: 71/193 Countries, 47/50 US States & 9/10 Canadian Provinces).

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