Cheap Flights to Caribbean from $76 (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 3 days ago

Tue, Apr 21 - Thu, Apr 30

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$202

Roundtrip

just found

Tue, Mar 24 - Tue, Apr 7

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$220

Roundtrip

found 18 hours ago

Tue, Mar 24 - Wed, Apr 1

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$234

Roundtrip

found 1 hour ago

Wed, Jun 3 - Thu, Jun 4

EWR

Newark Liberty Intl. Airport

SDQ

Las Americas Intl.

$246

Roundtrip

found 2 hours ago

Tue, Mar 24 - Wed, Mar 25

EWR

Newark Liberty Intl. Airport

AUA

Queen Beatrix Intl.

$255

Roundtrip

found 18 hours ago

Sat, May 9 - Sat, May 16

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$263

Roundtrip

found 5 hours ago

Mon, Jun 1 - Thu, Jun 4

EWR

Newark Liberty Intl. Airport

MBJ

Sir Donald Sangster Intl.

$278

Roundtrip

found 5 days ago

Fri, Apr 24 - Sat, Apr 25

JFK

John F. Kennedy Intl.

PUJ

Punta Cana Intl.

$280

Roundtrip

found 3 days ago

Wed, May 20 - Fri, Jun 5

JFK

John F. Kennedy Intl.

MBJ

Sir Donald Sangster Intl.

$286

Roundtrip

found 4 days ago

Fri, Oct 2 - Mon, Oct 5

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$287

Roundtrip

just found

Origin	Destination	Travel Dates	Flights From*
LGA	San Juan	April 25 to May 2	$182
EWR	San Juan	April 21 to April 30	$202
JFK	San Juan	April 10 to April 17	$255
EWR	Oranjestad	March 24 to March 31	$295
EWR	Santiago de los Caballeros	March 21 to March 26	$311
JFK	Punta Cana	April 11 to April 18	$334
JFK	Oranjestad	April 14 to April 29	$339
JFK	Santo Domingo	May 3 to May 5	$342
EWR	Nassau	June 5 to June 9	$349
EWR	Kingston	May 14 to May 20	$368
JFK	Nassau	May 11 to May 15	$377
JFK	Santiago de los Caballeros	April 22 to April 26	$378
JFK	Kingston	May 23 to May 28	$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*
LGA	Santiago de los Caballeros	March 13 to March 25	$418
JFK	Santiago de los Caballeros	March 14 to March 25	$426
EWR	Punta Cana	March 15 to March 19	$437
JFK	San Juan	March 15 to March 17	$455
JFK	Santo Domingo	March 15 to March 18	$460
JFK	Santo Domingo	March 15 to March 18	$460
JFK	Oranjestad	March 13 to March 17	$461
LGA	Nassau	March 15 to March 18	$477
EWR	Nassau	March 13 to March 20	$503
EWR	Montego Bay	March 14 to March 18	$514
JFK	Nassau	March 15 to March 21	$516
EWR	Santo Domingo	March 15 to March 18	$523
JFK	Montego Bay	March 14 to March 18	$603
JFK	Kingston	March 15 to March 22	$609
JFK	Punta Cana	March 15 to March 19	$652

*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

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

4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

Apr 29 - May 2

3 night stay

Boston (BOS) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • Coach

$1,270

per person

found 1 day ago

4.0-star property

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Apr 12 - Apr 18

6 night stay

Boston (BOS) to Nassau (NAS)

American Airlines • Non-stop roundtrip • Coach

$2,045

per person

found 1 day ago

4.0-star property

Hotel Riu Montego Bay - Adults Only - All Inclusive

May 31 - Jun 6

6 night stay

Boston (BOS) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach

$1,324

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! (1,009 reviews)

Nice hotel, but a bit pricey for what it was. My biggest complaint is that it was very loud. The automatic lights to the front of the

Reviewed on Mar 6, 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 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cable Beach and Pirates of Nassau Museum are located nearby.

8.6/10 Excellent! (2,319 reviews)

I had a garden view not worth the money

Reviewed on Mar 7, 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! (1,557 reviews)

Loved the location, walkable distance to many of the popular spots in Viejo San Juan. Has both a cafe and restaurant on property.

Reviewed on Mar 6, 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! (1,438 reviews)

Friendly and helpful

Reviewed on Mar 5, 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

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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 $652 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 $76 (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

Sunset at the Palms Resort - Adults Only - All Inclusive

Apr 29 - May 2

Boston (BOS) to Montego Bay (MBJ)

Hotel Riu Palace Paradise Island - Adults Only - All Inclusive

Apr 12 - Apr 18

Boston (BOS) to Nassau (NAS)

Hotel Riu Montego Bay - Adults Only - All Inclusive

May 31 - Jun 6

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