Traveling for less is very simple: you just have to be flexible about everything (NOT just dates). **The concept** is very simple, but **doing it** isn’t always simple for every trip. To find cheaper plane tickets, when it’s not possible to be flexible on the dates, be flexible on the destination at least… even only by having 2 or 3 options instead of just 1. It can save you literally hundreds of dollars so easily.
The best way to find a really cheap flight (when paying with cash or simple points, not lucrative 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 destinations with 2 very important basic caveats and the whole step-by-step process with screenshots if you need it.
How to find the cheapest destinations
It’s really very easy, like pretty much everything else related to travel. You just need to know how. Flytrippers will help!
Here are the simple steps (step-by-step screenshots are below):
- Go to Kiwi
- Input your departure airport
- Input “Anywhere” as your destination
- Choose a departure date (or date range)
- Choose one of the 3 options for the return
- Choose a return date
- Choose a return date range
- Choose a length of stay
- Click on “Explore”
- Sort by “Cheapest”
That will give you an interactive map (and a list) of the cheapest destinations to fly to on those specific dates (and for today’s specific search date too; teaser of the 2 caveats below because we often spot Mexico in the $300s roundtrip for example).

For more advanced searches, such as finding the cheapest destinations for a specific date, Flytrippers strongly recommends the Kiwi tool.
We don’t recommend it to book!!! We recommend it 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 and how to see the cheapest destinations.
We like Kiwi because it has more airline options and more filter options, but Google Flights has the same feature if you prefer.
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 necessarily 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 plane tickets is so simple: search often! Search early and often. Take the time.
So I want to reiterate that the prices really 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 necessarily 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.
Their site looks like literally every plane ticket search tool you’ve ever used in your life.

But it does have more advanced features!
Input your departure airport
Input your departure airport. I’ll use Montreal (YUL) for my example.

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. Starting in late 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.

Input “Anywhere” as your destination
Most travelers will input a specific destination, but if you want to see all your options, input “Anywhere” as your destination.

Choose a date or 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.

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

Choose one of the 3 options for return dates
For the return date, you have 3 options.
The first is to choose a specific date. The second is to do the same thing as you did for departure: a range of dates.

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.

Click on “Explore”
Click to launch the search.

Sort by “Cheapest”
As we already 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.

It shows you the cheapest destinations!

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.
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
- Skyscanner (for more booking sites)
- Airline website (to see if it’s the same price)
- Reward programs (to redeem points)
- 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!
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Summary
It’s easy to find the cheapest destinations for your plane tickets on specific dates with the Kiwi tool. You can search for all destinations at once and see the ones that are the cheapest (the cheapest **at that specific moment in time**)!
What would you like to know about finding the cheapest destinations 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: Kyrgyzstan (photo credit: Azamat E)