Cheap Flights to Caribbean from $77 (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 2 days ago

Tue, May 12 - Wed, May 13

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$197

Roundtrip

found 2 hours ago

Tue, Mar 24 - Wed, Apr 1

JFK

John F. Kennedy Intl.

SJU

Luis Munoz Marin Intl.

$216

Roundtrip

found 5 hours ago

Sun, Apr 12 - Wed, Apr 15

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$246

Roundtrip

found 1 hour ago

Sun, Oct 4 - Sun, Oct 18

EWR

Newark Liberty Intl. Airport

PUJ

Punta Cana Intl.

$246

Roundtrip

found 4 hours ago

Sun, May 31 - Thu, Jun 4

EWR

Newark Liberty Intl. Airport

SDQ

Las Americas Intl.

$246

Roundtrip

just found

Tue, Mar 17 - Thu, Mar 19

EWR

Newark Liberty Intl. Airport

AUA

Queen Beatrix Intl.

$266

Roundtrip

found 2 days ago

Sun, Apr 12 - Fri, Apr 17

EWR

Newark Liberty Intl. Airport

SJU

Luis Munoz Marin Intl.

$267

Roundtrip

found 2 hours ago

Mon, Jun 1 - Thu, Jun 4

EWR

Newark Liberty Intl. Airport

MBJ

Sir Donald Sangster Intl.

$278

Roundtrip

found 4 days ago

Mon, Mar 9 - Wed, Sep 30

JFK

John F. Kennedy Intl.

MBJ

Sir Donald Sangster Intl.

$279

Roundtrip

found 3 days ago

Fri, Apr 24 - Sat, Apr 25

JFK

John F. Kennedy Intl.

PUJ

Punta Cana Intl.

$280

Roundtrip

found 2 days ago

Origin	Destination	Travel Dates	Flights From*
LGA	San Juan	April 18 to April 21	$180
EWR	San Juan	April 8 to April 14	$195
EWR	Santo Domingo	May 31 to June 4	$246
JFK	San Juan	May 28 to June 4	$259
EWR	Punta Cana	May 10 to May 16	$260
JFK	Oranjestad	April 28 to May 6	$297
JFK	Montego Bay	May 4 to May 8	$298
JFK	Punta Cana	April 16 to April 19	$306
LGA	Piarco	March 20 to March 25	$308
JFK	Piarco	March 27 to April 4	$328
JFK	Santo Domingo	May 3 to May 5	$342
JFK	Santiago de los Caballeros	May 17 to May 17	$365
JFK	Kingston	May 15 to May 16	$403
JFK	West End	March 20 to March 24	$419
JFK	West End	March 20 to March 24	$419

*Prices include taxes and fees

Origin	Destination	Travel Dates	Flights From*
EWR	Montego Bay	March 14 to March 25	$323
EWR	Montego Bay	March 14 to March 25	$323
EWR	Piarco	March 14 to March 18	$358
JFK	Oranjestad	March 15 to March 18	$436
JFK	Oranjestad	March 15 to March 18	$436
EWR	Punta Cana	March 15 to March 19	$437
EWR	Punta Cana	March 15 to March 19	$437
JFK	Santo Domingo	March 15 to March 25	$437
JFK	Santo Domingo	March 15 to March 25	$437
EWR	Oranjestad	March 13 to March 17	$478
EWR	Santo Domingo	March 15 to March 25	$512
JFK	Nassau	March 15 to March 20	$532
EWR	Kingston	March 14 to March 23	$538
EWR	Kingston	March 14 to March 23	$538
JFK	San Juan	March 14 to March 23	$677

*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

May 14 - May 19

5 night stay

Boston (BOS) to Montego Bay (MBJ)

Spirit Airlines • Non-stop roundtrip • Coach

$572

per person

found 1 day ago

4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

May 9 - May 16

7 night stay

Boston (BOS) to Montego Bay (MBJ)

JetBlue Airways • Coach

Montego Bay (MBJ) to Boston (BOS)

Frontier Airlines • Coach

$1,593

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

$1,362

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! (1,008 reviews)

Staff was amazing and the property was incredible. Amazing historical building with great views and a perfect location. Perks like the wine and cheese hour were so nice and I wish I had a longer stay!

Reviewed on Mar 4, 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! (2,316 reviews)

My fourth time here i feel like home a few inconvenience upon checking in was very upset but the manager like always turned it in to a great experience once again i love British colonial

Reviewed on Mar 4, 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! (1,555 reviews)

Great location and price!

Reviewed on Mar 5, 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! (1,437 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

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Affordable cars to get you around town

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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 $677 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 $77 (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

May 14 - May 19

Boston (BOS) to Montego Bay (MBJ)

Sunset at the Palms Resort - Adults Only - All Inclusive

May 9 - May 16

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

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