Trip-planning mode: activate. From beaches to budget destinations, Kayak’s annual Travel Hacker Guide looks at millions of searches to pinpoint trending destinations in the new year. The 2020 installment won’t be released until January, but we got a sneak peek at the When to Fly list, highlighting the best deals on airfare month by month. Here are the destinations that’ll get you the best bang for your buck throughout the year. 

Aerial of Hapuna Beach State Park on Hawaii's Big Island.
Hapuna Beach State Park on Hawaii's Big Island © Kris S/Getty Images

January: Big Island, Hawaii

Hawaiian vacations are a great antidote for the post-holiday blues, and prices to the Big Island drop 38% in January, with a median airfare of US$336.

Air France A340 landing at Princess Juliana International Airport (PJIA) at sunset on St.Maarten.
A plane landing at Sint Maarten's Princess Juliana International Airport at sunset © Alain M. Duzant/500px

February: Sint Maarten

St. Martin’s Dutch counterpart, Sint Maarten has beautiful beaches and a celebrated food scene – and if you book in February, prices drop 35%, with median airfares of US$390. 

Close-up of boy surfing in big wave at Teahuopoo,Tahiti.
Big-wave surfing surfing at Teahuopoo, Tahiti © Nisa and Ulli Maier Photography/Getty Images

March: Tahiti 

In the heart of French Polynesia, Tahiti boasts black-sand beaches, a bustling capital city, and natural splendour aplenty. Flights there are never exactly cheap, but in March, the median airfare is US$891 – a 43% price drop. 

View of the Port at Nantucket Island - Massachusetts
The Port at Nantucket Island, Massachusetts © Jon Davison/Lonely Planet

April: Nantucket, Massachusetts 

Spring in New England isn’t quite bikini weather, but offseason beach towns have their own unique charms. See for yourself in April, when flights to the tiny island of Nantucket, just off Cape Cod, cost 34% less, with median airfare ringing in at US$447. 

May: Sint Maarten 

Statistically, Sint Maarten sees quite a bit of rain in May, so pack a poncho and you’ll be rewarded with a median airfare of $390 – a 23% price drop. 

June: Vail, Colorado 

Vail is best known for its skiing, but between the hiking, biking, and fly-fishing, this small Rocky Mountain town offers plenty of action year-round. Visiting in June for the arts festival? You should see a 27% price drop and a median airfare of $440. 

The sand dunes of Cape Cod at sunset
Summer on Cape Cod is a quintessential American experience © CO Leong/Shutterstock

July: Cape Cod, Massachusetts 

From cedar-shingled cottages to lobster dinners, summering on the Cape is a quintessential American experience. In-season flights are surprisingly reasonable too, with median airfares of US$339, a 39% price drop.

August: Cape Cod, Massachusetts 

By August, the cold waters of the Atlantic should warm up enough for a swim, so now's the time for that picturesque New England beach week. The flight prices are in your favour as well: median airfare is US$333, a 40% drop. 

Pier with tour ship sailboat Margaret Todd Windjammer and people boarding in summer, Bar Harbor, Maine.
A pier in Bar Harbor, Maine © Andriy Blokhin/Alamy Stock Photo

September: Bar Harbor, Maine 

The gateway to Acadia National Park, Bar Harbor is busiest from late June through August and again during fall-foliage season, but there's a sweet spot just after Labor Day, in early September, when the crowds thin out and the weather remains idyllic. Prices drop 31% then too, with a median airfare of $356. 

Exterior of the historic Cabildo building in Plaza de Mayo, Buenos Aires.
The historic Cabildo building in Plaza de Mayo, Buenos Aires © Ed-Ni-Photo/Getty Images

October: Buenos Aires, Argentina 

With dining, drinking, and dancing galore, Argentina’s capital and largest city is a no-brainer for night owls. October is one of the best times to be in the city – the weather’s warm, and flight prices drop 18% (though median fares are still US$947).  

Colourful facades on a narrow street in Cartagena.
A narrow street in Cartagena © Fotos593/Shutterstock

November: Cartagena, Colombia 

A historic gem on the Caribbean coast, Cartagena de Indias has a UNESCO-protected Old Town that’s perfect for strolling, especially in the shoulder season, when there’s less rain, fewer tourists, and better deals to be had all around. Look for airfares to drop by 41%, with a median price of US$389. 

December: Sint Maarten

You wouldn’t think trading snow for sand would be a budget-conscious holiday choice, but fares to 2020’s most surprising bargain destination also drop in December, when flights are 33% cheaper and median airfare is $486. 

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