If you’re looking forward to a warm, dreamy getaway this May, I’ve got good news for you – traveling to four of the most stunning Latin American destinations has never been cheaper (or easier).

Not only is airfare to these gorgeous cities at its yearly low but the weather is fantastic and the crowds have died down a bit since their winter peak – in short, there’s no better time to finally pull the trigger on that much-needed sunny escape.

At least, that’s what we discovered thanks to Kayak’s data-backed “Best Time To Travel” tool.

And below, you’ll find out exactly why those of you planning to go someplace amazing this upcoming month need to put Tulum, Sao Paolo, Bogota, and Santiago right on top of your bucket list.


If there’s one destination that’s just gotten infinitely cheaper and easier to visit, it’s Tulum, and that’s thanks to the newly opened Felipe Carrillo Puerto airport, which is easily accessible by many, many U.S hubs (check out these articles 1,2,3 to find out if your city’s one of them).

Tulum International Airport

In May, round-trip flights will start at just $234, and tickets, in general, will be at (or very near) their yearly low, so if you’re looking to get the best possible value out of your Tulum trip, you’ll need to book those tickets fast.

And with temperatures set to average around 27-32°C (80-90°F) this upcoming month, you’ll get to do just about everything you want – from long sunbathing sessions at Playa Paraíso to fascinating excursions around the local Mayan ruins.

Paradise Beach (Playa Paraiso) in Tulum

Sao Paolo

When most of us think about a trip to Brazil, our mind immediately goes to long (9+ hours), expensive flights that seem entirely out of reach.

And while the “long” part is still true, I’m here to tell you that as long as you time your visit right and are willing to make do without any fancy extra on-flight amenities, you can travel from the U.S. to Sao Paolo and back for just a little over $400 – not nearly as bad as what you might’ve though, right?

Ibirapuera Park skyline, Sao Paulo, Brazil

The best thing about visiting Sao Paolo in May, though, is the fact that you’ll actually be able to get the best of both worlds, pleasant 15-23°C (59-73°F) temperatures and uncrowded attractions that you can actually experience without having to fight off hordes of impatient tourists.


If flights in the $400, or even $200-something range aren’t in the budget for you, don’t worry – you can travel to one of Latin America’s most fascinating destinations and back for only $155.

Street in Bogota, Colombia

Colombia’s gorgeous capital also happens to be one of the cheapest tourist hubs in South America (at least compared to similar cities), with accommodation prices ranging between $22-$44 a night, so if keeping your travels economic is a main priority, this might be your perfect choice.

Keep in mind, though, that temperatures in the city this time of year are on the cooler side, between 10°C (50°F) and 19°C (66°F), which, while perfect for long sightseeing excursions, aren’t particularly ideal for those looking to get into that summery spirit.

Colonial-era dome and spires In Bogota


Both Kayak and Skyscanner have crowned May the cheapest time to travel from the U.S. to Santiago, and when you see the kind of discounts you’ll get just by moving your trip next month, you’ll want to book those tickets ASAP.

Round-trip flights will start at $299 – these are the same exact tickets that would sell for upwards of $615 during peak months (which, according to Kayak, are December and March).

Japanese Park in Santiago, Chile

And if it’s impossible for you to put together a trip to Chile on such short notice, June is actually the second-best time to travel to Santiago, which gives you a bit of extra time but with two downsides – the weather will get cooler and it’ll become roughly 10% more expensive to fly.

I also want to note that even in May, temperatures in Santiago aren’t particularly warm since it’s late fall in the country this time of year (think within the 46-64°F range) – so sun lovers, keep that in mind.

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