18 Caribbean Destinations under $400 Round Trip from New York This Fall

Find the best deals from New York City to the Caribbean this fall with a look at 18 destinations that can be reached for less than $400 round trip.

Hopper Editors - Oct. 26, 2017

Surely but slowly the islands of the Caribbean are transforming themselves into year-round holiday destinations; transcending the old categories of low-season and high and offering would-be tourists a truly tantalizing menu of sun, sea, sand, sumptuous cuisine and luxurious accommodations, no matter the month.

For New Yorkers thinking of an autumn break, this is a pretty golden opportunity. After all, what better way to cure the big city woes of the five boroughs than with a dose of steaming late summer sun on the beaches of the cays, or a lively helping of samba and reggae with rum doused on top?

If that’s got you thinking, then check out these 20 bargain deals for round-trip flights from New York City to the Caribbean this fall. Each flight was found using the Hopper Flight Explorer, which makes it possible to explore deals on tickets with search queries like "New York to the Caribbean" or "New York to Europe."

Find deals on flights from New York to the Caribbean using the Hopper Flight Explorer and see which destinations are on sale right now!

18. Fly to Cayman Brac, Cayman Islands, for as low as $391 round trip

Photo by Venson Kuchipudi/Flickr.

Tadpole-shaped Cayman Brac continues to hone its reputation as the most refined of the islands in this archipelago nation from amidst the salty swells of the western Caribbean Sea. Away from the sprawling mega resorts and super hotels of its big brothers to the southwest, it’s rather remote, untouched and local; a place perfect for diving enthusiasts looking to score a pirate wreck, or eco-tourists in pursuit of quietude on the bluffs. Given the small size of the island’s airport, direct connections from NYC are impossible here, but there are a wealth of bargain indirect flights on offer this fall.

17. Fly to Punta Cana, Dominican Republic, for as low as $386 round trip

Photo by Roozbeh Rokni/Flickr.

Our next gateway to the Dominican Republic is perhaps also our most important, precisely because it connects New York with one of the kingpins of all-inclusive holidaying in the whole Caribbean: the island’s eastern region of Punta Cana. So, if it’s butler service, spa facilities and swim-up bars you’re after then why not consider either JetBlue or Delta out of JFK, or United Airlines from Newark’s Liberty International, all of which run nonstop to Punta Cana in just over four hours.

The absolute cheapest flights from New York to Punta Cana are connecting flights with US Airways from Newark. Take a look at prices here.

16. Fly to Saint Martin for as low as $357 round trip

Photo by Aero Icarus/Flickr.

New Yorkers looking to join the fray of beachcombers, sunbathers, snorkelers, scuba divers and sailors on Saint Martin are spoiled for choice, with American Airlines, JetBlue and Delta all connecting the island with JFK. Other routes into town include the United Airlines route from Newark’s Liberty International and a number of other indirect departures out of LaGuardia. All flights land at the Princess Juliana International Airport, which is just a stone’s throw from the self-proclaimed Vegas of the Caribbean, Maho Village, where super casinos and nightclubs dominate the scene.

15. Fly to Providenciales, Turks and Caicos, for as low as $356 round trip

Photo by acin355/Flickr.

Late-summer and autumn honeymooners of New York pay attention, because this nonstop United Airlines flight from the Liberty International Airport in Newark to the island of Providenciales is your ticket to the much coveted luxury spots of the Turks and Caicos. Hailed as one of the most romantic destinations in the whole Caribbean, this archipelago nation comes complete with all the enviable sunsets and shimmering sand beaches you’d expect, not to mention one of the best developed arrays of all-inclusive, adult-only resorts in the region.

14. Fly to Santa Barbara de Samana, Dominican Republic, for as low as $353 round trip

Photo by CARLOS CHELA/Flickr.

Perched on the quieter coastal reaches of the Dominican Republic’s northern shores, the sleepy little local town of Santa Barbara de Samana may seem like an unlikely candidate for bargain flights from JFK this fall. But JetBlue are defying expectations, and with this three-hour-and-forty-minute connection going for around just $353 return, are transporting New Yorkers to this laid back post-colonial fishing town; perfect for those who want to balance relaxation and cultural immersion on their autumn holiday this year.

If you fly to Santa Barbara on a Wednesday and return to NYC on a Wednesday, your ticket will be $725 cheaper. Seriously.

13. Fly to Saint Croix, US Virgin Islands, for as low as $352 round trip

Photo by m01229/Flickr.

If you feel the temptation for one of the rum cocktails of the USVI’s St Croix rising this fall, then answer the call by booking a seat on one of the many indirect flight connections out of New York City to the island’s Henry E. Rohlsen Airport. Return fares come it at a tantalizing low of around $352 for much of the autumn period, while travelers have the pick of the bunch when it comes to carriers — to take American Airlines from EWR via MIA or United through San Juan and onto Christiansted?

12. Fly to Nassau, Bahamas, for as low as $343 round trip

Photo by Sky Noir/Flickr.

Crazy, culturally-mind-boggling Nassau was once the stomping ground of Blackbeard and co.; a pirate free state of lawless buccaneers and pistol waving sailors who wanted nothing but a good time. Fast forward to today and not that much has changed, except perhaps there’s now some super good deals on direct flights with Delta Airlines and JetBlue from JFK to the city’s Lynden Pindling International Airport, bringing New Yorker’s into the lively Caribbean fold for as little as $343 return! That isn’t even enough travel time to develop scurvy.

Find money-saving tips for booking your flights to Nassau and compare the offerings from Delta and JetBlue.

11. Fly to La Romana, Dominican Republic, for as low as $343 round trip

Photo by gafe/Flickr.

Whether you’re heading for the top-100s golf course of the Casa de Campo that carves its way through the sea of sugar plantations around La Romana, or the wealth of luxury Dominican resorts that cluster around the coastal hotspots of the country’s eastern shores, this direct flight with JetBlue Airways from JFK is the perfect ride. Bargain roundtrip tickets during the autumn low season can cost as little as $340, while travelers can expect to pay upwards of $400 for a seat in December.

10. Fly to Aruba for as low as $337 round trip

Photo by WanderingtheWorld/Flickr.

Imagine trading in a couple of those brisk autumn evenings with the chance to samba the night away under the southern Caribbean sun, tasting a cocktail of blue curaçao the same color as the sea that swells all around. Well now you can for as little as $337, on one of the direct flight connections run by either Delta or JetBlue Airways out of JFK. Don’t expect to be alone on the beaches though, because this Island far from the late-summer hurricane belt is a favorite of east coasters right up and down the seaboard.

Direct flights also run from Newark to Aruba on United for as low as $450 round trip. Find deals here.

9. Fly to Santiago, Dominican Republic, for as low as $336 round trip

Photo by Adam Jones, Ph.D. - Global Photo Archive.

Before heading out to the pristine Caribbean beaches that so famously dot the East Coast and Samana provinces of the DR, take some time to check out the original American Santiago (officially Santiago de los Caballeros). It’s surrounded by the rugged hills of the Cibao Valley, peppered with interesting historical buildings and enjoys tropical temperatures well into the low-80s for much of the autumn low season. What’s more, direct flight routes are run by JetBlue and Delta, straight out of New York’s JFK International.

8. Fly to Puerto Plata, Dominican Republic, for as low as $327 round trip

Photo by Belivehotels.com/Flickr.

In the build-up to Thanksgiving and with all the stresses of the holiday season just around the corner, there can be no better way to sooth the soul than with a quick stint in Puerto Plata. Hidden amidst the coves and bays of Dominica’s north shore, this little microcosm of off-the-beaten-track resorts and eye-watering backcountry represents a tropical escape like no other. What’s more, it’s home to some of the country’s most-coveted attractions; the remote Playa Grande; the multi-tiered waterfalls of Damajagua; the cannon-blasted Fuerte de San Felipe.

Search for and buy your ticket to Puerto Plata on a Friday and you'll save up to $107 on your ticket!

7. Fly to Saint Thomas, US Virgin Islands, for as low as $304 round trip

Photo by Edgar Barany/Flickr.

Travelers from New York won’t even need to pack their passport for this connecting flight out of the city’s LaGuardia Airport. After a stop off in Fort Lauderdale, passengers will arrive amidst the jungle-clad hills and emerald waters of Saint Thomas Island, the veritable gateway to the United States Virgin Islands. From here they’ll be free to explore the archipelago, dipping in and out of the warm autumn shore currents, sunning themselves on the sands and sampling the fiery concoctions of the islands’ Carib-American-style kitchen.

6. Fly to Montego Bay, Jamaica, for as low as $300 round trip

Photo by gogrimm/Flickr.

Whether you opt to stay among the party streets and touristic hubbub of Montego Bay itself or venture out to the remoter beaches and resorts laced along the strands of western Jamaica, this indirect flight connection is your perfect ticket into town. Prices in the region of $300 return are common from early October to late November, affording travelers the perfect opportunity to capitalize on the lower hotel rates of the autumn shoulder-season. All flights go via Miami, Florida and depart from Newark’s Liberty International Airport.

Book your tickets from Newark Liberty to Montego Bay on a Friday and you can save up to $94 on each ticket!

5. Fly to Port of Spain, Trinidad and Tobago, for as low as $292 round trip

Photo by neiljs/Flickr.

Are the brown and yellow hues of Central Park getting you down? Is that late fall chill leaving you melancholy in the evenings? Then spice up those autumnal days with a dash of color and festivity, Trinidad and Tobago style. For around just $292 return, passengers from Newark’s Liberty International (on United Airlines non-stop) or New York’s JFK (with American Airlines and a stopover in Miami) can transport themselves to the samba-loving, sun-drenched city of Port of Spain, where rum punches flow continuously and the party never ends!

4. Fly to George Town, Cayman Islands, for as low as $287 round trip

Photo by rcbodden/Flickr.

Fares on JetBlue’s nonstop route from New York’s JFK airport to George Town’s Owen Roberts International on the island of Grand Cayman dip to their yearly low between September and early-November, making an off-season jaunt through the pearly Caribbean sands and sleepy towns of this British Overseas Territory a tempting possibility for many a New Yorker this fall. The flight takes just under four hours one-way and drops passengers in the capital at George Town — the perfect base from which to explore the paradisal outer islands of Brac and Little Cayman.

Travelers can save up to $48 per ticket just by booking their flight on a Thursday! Find more money-saving tips in Hopper's flight report.

3. Fly to Aguadilla, Puerto Rico, for as low as $280 round trip

Photo by Jaime Olmo/Flickr.

Surfers stuck in the Big Apple for the fall will no doubt welcome this super-cheap air connection to Aguadilla in Puerto Rico, which sits just a stone’s throw from the famed reef breaks at Jobos and the rare beach breaks at Crash Boat. There are two main options open to travelers looking to make the trip: United Airlines’ nonstop flight out of Newark’s Liberty International and the cheaper Spirit Airlines connection from the city’s LaGuardia Airport, stopping over in Fort Lauderdale. Just make sure to double check how much extra Spirit will charge you in additional fees using the Hopper Airline Fees Calculator before you pick an airline.

2. Fly to Santo Domingo, Dominican Republic, for as low as $277 round trip

Photo by Dianne Rosete/Flickr.

One of the Caribbean’s largest nations and unquestionably one of its most culturally and naturally diverse, the Dominican Republic dominates the eastern half of Hispaniola in a patchwork of verdant inland mountains, roaring jungle rivers, wild fields of untamed mangroves and, of course, a veritable wealth of crushed-coral colored beaches and turquoise waters. But all that aside, New Yorker’s flying in from Newark’s Liberty International will probably feel most at home in the bustling capital at Santo Domingo, where Dominica’s post-colonial wonders coalesce in the crevices of its most vibrant modern cityscape.

The cheapest tickets from New York to Santo Domingo are connecting flights with US Airways from Newark Liberty.

1. Fly to San Juan, Puerto Rico, for as low as $253 round trip

Photo by dameetch/Flickr.

This nonstop flight with JetBlue airlines is the New Yorker’s ticket to the sun, sand and tropical terrain of Caribbean Puerto Rico this fall. Passengers will arrive in the midst of the island’s laid-back low-season, when the popular sand stretches of San Juan, such as Condado and the Isla Verde, are enjoying temperatures in the mid-80s without any of the bustling crowds of winter. This also means lower hotel rates and the pick of the best scuba diving spots, snorkelling reefs and surfing swells the island has to offer. for as low as $253 return, what’s not to like?

Find more deals to Caribbean destinations from New York using the Hopper Flight Explorer!

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