With just $499 to spend on flights, you can still book the trip of a lifetime this year … even though airfare is (almost universally) up across the board.
How? By booking flights at the right time and on the right days – and also targeting airlines and destinations that have lots of competition.
This is the pattern we've seen over and over again. I'm part of a team of 10 flight deal analysts who are constantly searching for cheap flights and points and miles award deals for our Thrifty Traveler Premium flight deal alert subscribers, and we sent close to a hundred flight deals in June, including all of the fares and flight deals I'll show you below.
3 Steps to Find the Best International Flight Deal
Here's what you can do to get the best deal right now.
First, aim for shoulder season. Shoulder season is the months directly before and after peak season, which is usually summer. So, shoulder season in the northern hemisphere is typically April-May and September-October. In the southern hemisphere, it's October-November and March-April.
Look at this flight deal from Orlando (MCO) to Santiago, Chile (SCL) as an example. If you want to book in December or January (Chile's peak summer), you'll pay peak summer prices.
But … if you book in November, during Chile's springtime, you'll pay a fraction of that.
Second, aim for the middle of the week. You probably noticed it in the fare above, and you'll see it again in the fare below. The single best thing you can do is book flights mid-week – Tuesdays and Wednesdays – to get the best deals.
Besides getting the best fares, I like to travel mid-week to maximize my vacation time. Having a full Saturday and Sunday off in a new place is awesome. You don't have to worry about traveling on frenetic (expensive) Sundays, and you can really enjoy your trip through the weekend and into the next week. This roundtrip itinerary to Bergen (BGO) shows a stellar roundtrip rate if you're open to mid-week flights.
Third, seek out competition. This works in multiple ways. To save, you should look for competitive markets – both for your departure and destination cities. This flight deal to the incredible city of Helsinki, Finland (HEL) is a good example of this. Many of the cities you see listed here have several airlines offering flights to Europe, creating competitive pricing pressure and driving fares into the $400s. (These are also mostly shoulder season and mid-week fares, too.)
But HEL is a competitive airport itself, too. Airlines like Finnair, British Airways, Aer Lingus, KLM, Air France, Lufthansa, Icelandair, and SAS all serve the airport, and they all want to be the one to take you there. That's how you get fares like these.
When the airlines fight for your business, travelers win! But it gets even better, because not all competition is created equal. What you really want is a flight deal to a place with “low-cost” competition.
All three of the examples above are perfect examples of this. The Santiago deal? Low-cost competition from LATAM. The Bergen and Helsinki deals? Low-cost competition from Icelandair and SAS.
This deal below is yet another: Roundtrip flights to Dublin (DUB) in August in the $400s roundtrip. How is this possible? Well, Ireland's flag carrier Aer Lingus is offering cheap nonstop flights to all of these cities, so Air Canada and United had to jump in with their own low fares to match or beat out many of Aer Lingus's low-cost fares.
To review, I'd always recommend aiming for shoulder season, the middle of the week, and competitive markets to get the best price on an international flight this year.
Other (Warmer) Places to Go Under $499 Roundtrip
Most of my examples above were to cooler climates, but if you're more of a beach-goer, I've got you!
For flights to Central America, the Caribbean, and Mexico this fall and winter, you don't have to spend an arm and a leg to book your trip … even to bougie destinations like St. Kitts and Nevis (SKB).
This JetBlue fare (and more than 20 others we included in our Thrifty Traveler Premium flight deal alerts last month) is part of the reason why fares to SKB got so low. JetBlue keeps fares low, and the other airlines have to follow. Plus, if you live near Fort Lauderdale (FLL) or New York (JFK), you can fly nonstop on JetBlue, too! This is a great example of how a low-cost competitor can drive down prices.
The same can be said for flights to the Cayman Islands (GCM), including this long list of airports where American Airlines and Delta slashed rates to compete, bringing passengers from these airports to Grand Cayman starting at just $286 roundtrip this winter. Even more than competition, though, you can get these awesome fares (many of which are in peak winter season) by booking in the middle of the week.
Want to fly from Friday to Sunday? You're going to pay triple these fares that mostly take off on Tuesdays and Wednesdays.
This next flight deal to Cancún, Mexico (CUN), combines all three major ways to save on flights. CUN is one of the most competitive airports on the continent and includes flights from every single airline, from the low-cost carriers to the full-service ones. But many of the best fares here can be found in late fall – outside of hurricane season, but before the holidays and peak season begins in Mexico. And, of course, the lowest of these fares depart on Tuesdays and Wednesdays, too.
You can and should look around the world to see where these three strategies can take you, because cheap airfare like these are still out there!
Bottom Line
If you book shoulder season flights, aim for flights in the middle of the week, and look at destinations with lots of competing airlines, you stand to save a ton on flights this year.
Those strategies mean you can fly to destinations like the Cayman Islands, Norway, and many more for less than $499 roundtrip.







