Question 1

How much is the cheapest flight to Caribbean?

Accepted Answer

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 $130. 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.

Question 2

Which airlines fly to Caribbean?

Accepted Answer

Pack your bags and jet off with any of the 15 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.

Question 3

What is the cheapest month to fly to Caribbean?

Accepted Answer

Spend more money on great adventures rather than airfares by zipping off to Caribbean in January. 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.

Question 4

How can I check my flight status to Caribbean?

Accepted Answer

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.

Question 5

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

Accepted Answer

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 $130. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Question 6

Why should I book my flight to Caribbean with Travelocity?

Accepted Answer

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.

Question 7

How much is a flight to Caribbean on average?

Accepted Answer

Plane tickets for roundtrip flights to Caribbean cost between $130 and $512 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.

Question 8

What can I expect on a flight to Caribbean?

Accepted Answer

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.

Origin	Destination	Travel Dates	Flights From*
EWR	San Juan	February 3 to February 5	$152
EWR	San Juan	February 3 to February 5	$152
JFK	San Juan	February 24 to March 4	$162
EWR	Montego Bay	February 3 to February 10	$248
EWR	Santo Domingo	March 2 to March 11	$260
EWR	Santiago de los Caballeros	January 31 to February 7	$260
EWR	Nassau	February 21 to February 28	$272
EWR	Nassau	February 21 to February 28	$272
JFK	Nassau	January 31 to February 7	$289
JFK	Santiago de los Caballeros	March 16 to March 17	$294
JFK	Montego Bay	February 21 to February 28	$325
LGA	Kingston	February 2 to February 5	$354
JFK	West End	February 9 to February 11	$399
JFK	West End	February 9 to February 11	$399
JFK	Kingston	March 23 to April 1	$410

Origin	Destination	Travel Dates	Flights From*
EWR	San Juan	January 18 to January 27	$168
JFK	San Juan	January 17 to January 30	$240
LGA	Oranjestad	January 17 to January 31	$336
JFK	Oranjestad	January 17 to January 31	$343
EWR	Nassau	January 17 to January 20	$366
EWR	Nassau	January 17 to January 20	$366
LGA	Montego Bay	January 17 to January 23	$366
LGA	Santiago de los Caballeros	January 18 to February 27	$372
JFK	Santiago de los Caballeros	January 18 to January 22	$383
LGA	Punta Cana	January 18 to January 25	$426
JFK	Punta Cana	January 17 to January 20	$436
JFK	Santo Domingo	January 17 to January 24	$437
JFK	Montego Bay	January 18 to January 22	$462
JFK	Kingston	January 18 to January 27	$512
JFK	Kingston	January 18 to January 27	$512

Cheap Flights to Caribbean from $62 (2026/2027)

Travelers

Jet to one of Caribbean's top cities

Santo Domingo

Punta Cana

St. Thomas

Willemstad

How Much Does it Cost To Fly To Caribbean?

Best Caribbean Flight and Hotel Packages

Ola Boutique Hotel

Mar 22 - Mar 26

Boston (BOS) to San Juan (SJU)

San Juan (SJU) to Boston (BOS)

Blue Seas Two Unity Hall

Feb 18 - Feb 22

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

Alamanda Cottage at Serenity

Jan 31 - Feb 7

Boston (BOS) to Montego Bay (MBJ)

Montego Bay (MBJ) to Boston (BOS)

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