10 Unexpectedly Great Deals on Flights from Boston

Use the Hopper Flight Explorer to discover 10 unexpectedly great deals on international flights from Boston!

Hopper Editors - Oct. 26, 2017

When the clean and collected cityscape of Boston gets just a little too much, many New England locals head for the city’s Logan International Airport, where they hop on flights to far flung destinations or catch domestic connections to some of America’s more popular holidaying spots. With JetBlue, Delta, US Airways, American Airlines and a whole host of other carriers flying regular routes out of town, it’s rarely hard to come up with somewhere exciting to go.

Indeed, here’s a list of some of the most unexpected destinations to which travelers have found good deals using the newly launched Hopper Flight Explorer, which makes it easy to discover new destinations through its ability to search for flights to regions, countries and even entire continents. So have your passport at the ready!

Change your origin airport, choose a destination or enter your dates to discover more deals using the Hopper Flight Explorer!


Photo by cclark395/Flickr.

1. Sunning in the heart of Mesoamerica with Spirit to San Jose, Costa Rica, for $319 round trip


Photo by stinkenroboter/Flickr.

"Do you know the way to San Jose?" Yes, actually we do! And we don’t mean the Californian city of Silicon Valley, but rather the sun-drenched capital of Costa Rica in the heart of Central America. From Boston, it’s now easily accessible on Spirit Airlines, with stopovers at Myrtle Beach and Fort Lauderdale, Florida. The trip takes just a little over eight hours and we’ve even managed to find return tickets for as little as $319!

2. Heading down south for a dose of sun and sea with Delta to George Town in the Cayman Islands for only $330 round trip


Photo by Ricymar Photography/Flickr.

Perched out in the central swells of the Caribbean Sea, the Cayman Islands are a patchwork of Robinson Crusoe beaches and world-class diving spots all oozing with that quintessentially tropical vibe and a curious lingering flavor of British colonialism that’s at once relaxing and alluring in equal measure. Today Boston natives can be enjoying the southern sun in no time, by taking this single-stop connection with Delta to George Town’s Owen Roberts International Airport via way of Atlanta. Don’t forget the sunscreen!

3. Going into the wild with Delta to Anchorage, Alaska, for $385 round trip


Photo by Alaskan Dude/Flickr.

From all sides the towering peaks of Alaska’s windswept, snow-tipped Coast Mountains peer down onto the little city of Anchorage, reminding visitors that while this town may have the 7-11s and sleepy suburbs, it is wholly and indelibly in the grip of the wild. Just a stone’s throw from town, wildlife-spotting and hiking opportunities abound amidst the Chugach peaks, while there’s also some great ski fields and biking parks to enjoy. For the budding nature explorer, this connection from Boston is the perfect choice, taking just 10 hours from start to finish and costing as little as $388 on Delta with a stop in Minneapolis!

4. See the mid-Atlantic with SATA to Ponta Delgada, Portugal, for $395 round trip


Photo by Silvain de Munck/Flickr.

Pretty Ponta Delgada is the traveler’s gateway to the Portuguese Azores; a pin point archipelago, washed over by the mid-Atlantic swells more than 850 miles west of mainland Europe. It’s a land of monstrous volcanic calderas and verdant growing valleys, soaring coastal cliffs and sleepy post-colonial cities where the explorers of the New World would once restock their ships and rest before the final push on to the Americas. $395 gets you a return ticket from Boston, taking just five hours and flying direct to the island’s Joao Paulo II Airport.

5. Enter the Caribbean with American to St Martin for $438 round trip


Photo by takot/Flickr.

Another of the more unexpected routes from Boston to the Caribbean, this American flight has one stopover in Miami and will drop visitors in the massive Princess Juliana International Airport – one of the best places to catch connecting flights to the other tropical islands in the region! But, if you fancy loitering a little while and exploring curious St Martin, with its smattering of Franco-Dutch eateries and 37 breath-taking beachfronts, then that’s all good too!

6. Discover the Caribbean’s largest metropolis with JetBlue to Santo Domingo, DR, for $433 round trip


Photo by Dianne Rosete/Flickr.

Yes, you did read that correctly! For around just $433 you could be exploring one of the most historically rich cities in the whole Caribbean, wandering amidst its romantic church facades, spying out its Spanish palaces and navigating the winding web of cobbled roads that form its 15th-Century Zona Colonial. The route is managed by JetBlue, runs daily, takes approximately four hours from start to finish, and best of all, flies nonstop from Boston, Massachusetts!

7. Wander ancient streets and see post-colonial churches with Avianca to Quito, Ecuador, for $497


Photo by Yassef/Flickr.

Quito soars above most other capital cities in South America, both in style and in geography. It’s perched more than 2,800 meters above sea level, in the misty foothills of the Andes Mountains, and is home to the largest historical old town district on the continent. Bursting with Spanish churches and stucco monasteries, this is a place that still very much lives up to its UNESCO heritage tag, while for just $497, visitors from Boston will be here in under 15 hours!

8. Find your inner Jules Verne with Icelandair to Reykjavik, Iceland, for $586


Photo by christine zenino/Flickr.

Those arriving in Iceland’s capital by air can gaze down on the red and navy roofs of the charming Tjornin old town that awaits them below, a place of enchanting little coffee shops and stoic Icelander beer bars. In the distance, the great valley creases and glacial massifs of the Snaefellsjokull National Park loom on the horizon; a reminder that Iceland is an outdoorsy dream-come-true! Today, it’s possible to arrive here on Icelandair direct from Boston for around just $586 in just under six hours!

9. Discover a hidden gem with SATA to Lisbon, Portugal, for $625 round trip


Photo by szeke/Flickr.

Lisbon is one of the most criminally under visited cities in Southern Europe, as it’s often overlooked in favor of its more glamorous Spanish neighbors. But while Lisbon goes underappreciated by the tourism market, visitors to Lisbon are rewarded with low prices and plenty of authentic charm. Bostonians can reach Lisbon direct on SATA in just six hours for only $625 round trip. Not a bad price to pay to discover one of Europe’s hidden gems.

10. Meet Europe with Turkish Airlines to Barcelona, Spain, for $747 round trip


Photo by Don McCullough/Flickr.

While the romantic downtown of Barcelona – with its gothic churches and Gaudi architecture – may be the final destination on this flight out of Boston, passengers will also get the opportunity to explore one of Europe’s hippest, biggest and most happening cities during a single stop in Istanbul! The connection is operated by Turkish Airlines, takes just over 17 hours with layovers included and can be scooped for as little as $747 return! It’s the perfect introduction to Europe!

Change your origin airport, choose a destination or enter your dates to discover more deals using the Hopper Flight Explorer!

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