Cheap Flights to Caribbean from $81 (2026/2027)| Travelocity

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Jet to one of Caribbean's top cities

Bayahibe Beach featuring general coastal views

Punta Cana

Flights

How Much Does it Cost To Fly To Caribbean?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Mar 17 - Thu, Apr 2

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$170

Roundtrip

found 5 days ago

Tue, Apr 21 - Fri, Apr 24

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$202

Roundtrip

just found

Mon, Mar 23 - Fri, Apr 3

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$230

Roundtrip

found 5 hours ago

Tue, Mar 24 - Wed, Apr 1

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$231

Roundtrip

found 3 hours ago

Sun, May 17 - Thu, May 21

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$246

Roundtrip

found 2 hours ago

Thu, Jun 4 - Fri, Jun 5

EWR

Newark Liberty Intl. Airport

SDQ

Las Americas Intl.

$246

Roundtrip

found 5 hours ago

Tue, Mar 24 - Wed, Mar 25

EWR

Newark Liberty Intl. Airport

AUA

Queen Beatrix Intl.

$255

Roundtrip

found 2 days ago

Sun, Apr 12 - Wed, Apr 22

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$267

Roundtrip

found 4 hours ago

Fri, Apr 24 - Sat, Apr 25

JFK

John F. Kennedy Intl.

PUJ

Punta Cana Intl.

$280

Roundtrip

found 5 days ago

Wed, May 20 - Fri, Jun 5

JFK

John F. Kennedy Intl.

MBJ

Sir Donald Sangster Intl.

$286

Roundtrip

found 6 days ago

Wed, Apr 22 - Wed, Apr 29

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$287

Roundtrip

just found

Origin	Destination	Travel Dates	Flights From*
LGA	San Juan	April 18 to April 24	$182
EWR	San Juan	April 21 to April 24	$202
JFK	San Juan	April 11 to April 15	$278
EWR	Montego Bay	April 27 to May 6	$298
EWR	Montego Bay	April 27 to May 6	$298
JFK	Montego Bay	April 13 to April 23	$302
EWR	Santiago de los Caballeros	March 23 to March 26	$311
JFK	Piarco	June 7 to June 18	$328
JFK	Punta Cana	April 10 to April 17	$334
JFK	Santo Domingo	May 16 to May 17	$345
EWR	Kingston	May 14 to May 20	$368
JFK	Santiago de los Caballeros	April 22 to April 26	$378
JFK	Kingston	May 12 to May 16	$446
JFK	West End	April 1 to April 14	$562
JFK	West End	April 1 to April 14	$562

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
EWR	Montego Bay	March 14 to March 18	$325
EWR	Montego Bay	March 14 to March 18	$325
EWR	Piarco	March 15 to April 18	$428
EWR	Nassau	March 15 to March 18	$431
JFK	Santiago de los Caballeros	March 15 to April 3	$431
JFK	Santiago de los Caballeros	March 15 to April 3	$431
EWR	Punta Cana	March 15 to March 19	$437
EWR	Santiago de los Caballeros	March 15 to March 17	$462
JFK	Santo Domingo	March 15 to March 19	$492
JFK	Santo Domingo	March 15 to March 19	$492
EWR	Kingston	March 15 to March 21	$507
EWR	San Juan	March 14 to March 18	$510
EWR	San Juan	March 14 to March 18	$510
JFK	San Juan	March 13 to March 18	$529
EWR	Santo Domingo	March 15 to March 19	$596

*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.

3.5-star property

Silver Creek Resort

Apr 14 - Apr 19

5 night stay

Boston (BOS) to Montego Bay (MBJ)

Spirit Airlines • Non-stop • Coach

Montego Bay (MBJ) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

$551

per person

found 1 day ago

4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

May 20 - May 25

5 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • Coach

$1,263

per person

found 1 day ago

4.0-star property

Hotel Riu Palace Aquarelle - All Inclusive

May 20 - May 25

5 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • Coach

$1,436

per person

found 1 day ago

Don't see what you're looking for?

See all available trips from Boston to Caribbean

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Travelers ❤️ These Caribbean 🏨

Hotel El Convento

100 Cristo St San Juan

Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.

9/10 Wonderful! (1,011 reviews)

Perfect location across from the Cathedral. A beautiful historic hotel.

Reviewed on Mar 7, 2026

British Colonial - Nassau

Number One Bay St Nassau

Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.

8.6/10 Excellent! (2,324 reviews)

Overall it was good, but attention to detail could be better. We are a family of 4 in a double room city view and there were only 2 towels and not enough hangers. We had to ask for a hair dryer even though it was listed. There aren't enough towel bars,very little space to hang things and the shower ...

Reviewed on Mar 9, 2026

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico

Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.

9/10 Wonderful! (1,563 reviews)

Clean room wasn’t helpful when trying to get change. Great location.

Reviewed on Mar 9, 2026

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The Reef at Atlantis

Paradise Beach Drive Paradise Island New Providence

Book a stay at this luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.

9/10 Wonderful! (1,442 reviews)

Had great time Family of 4 with 2 kids Amazing place to spend time

Reviewed on Mar 9, 2026

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More Ways To Wander Caribbean

Caribbean Hotels

Find the perfect hotel after your flight

Caribbean Vacation Rentals

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Affordable cars to get you around town

Caribbean Vacations

Save more by combining flights, hotels and cars

Frequently asked questions

How much is the cheapest flight to Caribbean?

Your next vacation doesn't have to make a huge dent in your budget. During the last seven days, the cheapest roundtrip flight to Caribbean cost $170. Find a cheap ticket and spend the money you save on cool experiences. This price was available on Travelocity for flights to Caribbean departing within the next year. Prices and availability are subject to change. Additional terms apply.

Which airlines fly to Caribbean?

Pack your bags and jet off with any of the 20 airlines that fly to Caribbean. Make a booking with popular air carrier, Sunrise Airways. It has approximately 43 flights per month to Santo Domingo, Caribbean's premier city, so finding a fare that suits should be a snap.

What is the cheapest month to fly to Caribbean?

Spend more money on great adventures rather than airfares by zipping off to Caribbean in March. This is the best-priced month to jet out to this place according to Travelocity's direct return flight demand from January to December last year. Browse through our range of flights and enjoy a change of scenery without emptying your bank account.

How can I check my flight status to Caribbean?

Check for updates on your flight to Caribbean, make changes and much more from our "Trips" customer portal. Found at the top right of our homepage, it's your gateway to viewing your bookings. Just log in or open an account in seconds. Savvy wanderers can also take advantage of the Travelocity app. You'll get real-time trip updates, along with the ability to book hotels, rental cars and activities while you're on the go. If you have friends or family flying with you, it's also a quick way to share travel info with each other.

How do I find the best deals on flights to Caribbean?

It's always good to book ahead of schedule, and if possible, avoid traveling during the busy tourist season. Another great way to save is by hitting the "Flexible dates" box at the top of the page after searching for your flights. This will show you ticket prices for nearby days. In the last seven days, the lowest price for a return flight to Caribbean was $170. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Why should I book my flight to Caribbean with Travelocity?

Pack your case and get set to take off with Travelocity. It's our job to find you fantastic deals on cheap flights to Caribbean. Whether you want flexible airfares with plenty of wiggle room or cheap family flights on budget carriers, we've got what you need.

How much is a flight to Caribbean on average?

Plane tickets for roundtrip flights to Caribbean cost between $170 and $596 in the last seven days. The moment you find an incredible deal, lock it in and get ready to set off on the getaway of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

What can I expect on a flight to Caribbean?

The duration of your flight and whether you're flying with a full-service or low-priced airline play a major role. If you're searching for long-haul flights to Caribbean, drinks, food and entertainment will often be included. Want cheap flights for family vacations? You'll save with budget carriers. These airlines usually don't have as many inclusions, so be prepared to pay for food and drinks.

Cheap Flights to Caribbean from $81 (2026/2027)

Travelers

Jet to one of Caribbean's top cities

Punta Cana

St. Thomas

Montego Bay

St. John

Nassau

How Much Does it Cost To Fly To Caribbean?

Best Caribbean Flight and Hotel Packages

Silver Creek Resort

Apr 14 - Apr 19

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

Sunset at the Palms Resort - Adults Only - All Inclusive

May 20 - May 25

Boston (BOS) to Montego Bay (MBJ)

Hotel Riu Palace Aquarelle - All Inclusive

May 20 - May 25

Boston (BOS) to Montego Bay (MBJ)

Travelers ❤️ These Caribbean 🏨

Hotel El Convento

British Colonial - Nassau

Hotel Rumbao, a Tribute Portfolio Hotel

The Reef at Atlantis

More Ways To Wander Caribbean

Frequently asked questions