HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$152+ Cheap flights from Worcester, MA (ORH) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
May 1 — May 81
Fri 5/1
Fri 5/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Worcester to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Worcester to Caribbean Islands

Cheapest flights from Worcester to Caribbean Islands
Explore the most affordable flight options available from Worcester to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.

This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:29 pm
ORH
-
SJU
1 stop7h 18m
American Airlines
Thu 11/266:25 am
SJU
-
ORH
1 stop9h 39m
American Airlines
Deal found 3/27$298
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:43 pm
ORH
-
SJU
2 stops19h 12m
American Airlines
Sat 9/127:05 pm
SJU
-
ORH
2 stops26h 02m
American Airlines
Deal found 3/27$327
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:43 pm
ORH
-
SJU
2 stops15h 26m
American Airlines
Sat 8/226:00 am
SJU
-
ORH
1 stop10h 52m
American Airlines
Deal found 3/27$342
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:24 pm
ORH
-
MBJ
2 stops22h 53m
Delta
Wed 4/294:32 pm
MBJ
-
ORH
2 stops23h 11m
Delta
Deal found 3/29$357
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:16 pm
ORH
-
STT
2 stops22h 44m
American Airlines
Tue 7/142:41 pm
STT
-
ORH
2 stops26h 10m
American Airlines
Deal found 3/27$367
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:18 pm
ORH
-
SJU
2 stops16h 21m
American Airlines
Tue 7/147:00 am
SJU
-
ORH
1 stop9h 51m
American Airlines
Deal found 3/31$367
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:43 pm
ORH
-
PUJ
1 stop16h 22m
American Airlines
Wed 11/42:25 pm
PUJ
-
ORH
2 stops25h 39m
American Airlines
Deal found 3/29$369
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:15 pm
ORH
-
SDQ
2 stops21h 09m
Delta
Tue 5/122:49 pm
SDQ
-
ORH
2 stops24h 44m
Delta
Deal found 3/31$371
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:24 pm
ORH
-
PUJ
2 stops21h 08m
Delta
Sat 5/23:49 pm
PUJ
-
ORH
2 stops24h 54m
Delta
Deal found 3/28$373
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:16 pm
ORH
-
STT
2 stops20h 32m
American Airlines
Thu 7/94:50 pm
STT
-
ORH
2 stops24h 01m
American Airlines
Deal found 3/27$376
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:16 pm
ORH
-
STT
2 stops17h 47m
American Airlines
Mon 7/274:50 pm
STT
-
ORH
2 stops24h 01m
American Airlines
Deal found 3/27$381
This American Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:39 pm
ORH
-
SJU
1 stop7h 26m
American Airlines
Fri 5/16:00 am
SJU
-
ORH
1 stop8h 14m
American Airlines
Deal found 3/30$382

Find flight deals from Worcester to Caribbean Islands

Keep the following information in mind while searching for Worcester to Caribbean Islands flight deals. Data was last updated April 1, 2026.

Round-trip from

$327
(American Airlines)

One-way from

$152
(Delta)

Popular in

December

Cheapest in

January

Average price

$309
From Worcester to Caribbean Islands
Search Deals
One-way flight from Worcester to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 1, 2026.
Use the filters below to find and compare flights from Worcester to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Fri 4/24

5:24 pm-3:17 pm

2 stops22h 53m

Montego Bay Sangster Intl

Wed 4/29

4:32 pm-4:43 pm

2 stops23h 11m

$357

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Thu 5/7

4:15 pm-1:24 pm

2 stops21h 09m

Santo Domingo Las Americas

Tue 5/12

2:49 pm-3:33 pm

2 stops24h 44m

$371

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Mon 4/27

5:24 pm-1:21 pm

2 stops19h 57m

Punta Cana

Sat 5/2

3:49 pm-4:43 pm

2 stops24h 54m

$373

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sun 4/26

5:24 pm-2:32 pm

2 stops21h 08m

Punta Cana

Sat 5/2

3:49 pm-4:43 pm

2 stops24h 54m

$373

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Sat 5/9

2:39 pm-1:30 pm

2 stops22h 51m

Oranjestad Reina Beatrix

Sat 5/16

5:25 pm-2:14 pm

2 stops20h 49m

$384

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

Fri 6/26

5:18 pm-11:57 am

2 stops18h 39m

Saint Thomas Island Cyril E King

Tue 7/7

4:50 pm-4:51 pm

2 stops24h 01m

$385

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 9/6

7:43 pm-2:55 pm

2 stops19h 12m

San Juan Luis Munoz Marin Intl

Sun 9/13

4:10 pm-9:07 pm

2 stops28h 57m

$386

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 4/13

2:39 pm-10:05 pm

1 stop7h 26m

San Juan Luis Munoz Marin Intl

Fri 4/17

6:00 am-2:14 pm

1 stop8h 14m

$388

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 6/29

5:18 pm-9:39 am

2 stops16h 21m

San Juan Luis Munoz Marin Intl

Tue 7/14

7:14 pm-4:51 pm

2 stops21h 37m

$394

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Thu 6/11

5:18 pm-3:42 pm

2 stops22h 24m

Simpson Bay Princess Juliana

Mon 6/15

2:53 pm-4:53 pm

2 stops26h 00m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 52 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Worcester to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Worcester with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Worcester to Caribbean Islands

What is the cheapest month to book a flight from Worcester, Massachusetts to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $93). Flying from Worcester, Massachusetts to Caribbean Islands in October is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Worcester to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Worcester to Caribbean Islands?

    Worcester (ORH), located 3.8 mi from the city center, is the airport you fly out of when you book flights from Worcester to Caribbean Islands.

  • How long is the flight from Worcester, Massachusetts to Caribbean Islands?

    There are many flights that can get you from Worcester, Massachusetts to Caribbean Islands in 19h 12m. Fly via American Airlines or Delta to get the fastest option. Worcester, Massachusetts and Caribbean Islands are separated by a distance of 1681 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Worcester, Massachusetts to Caribbean Islands?

    The most popular route from Worcester, Massachusetts to Caribbean Islands is Worcester - San Juan Luis Munoz Marin Intl. You may also consider Worcester - Oranjestad Reina Beatrix or Worcester - Castries George F. L. Charle.

  • Can I find deals for flights from Worcester to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Worcester to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Worcester to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Worcester to Caribbean Islands.

  • Can I find deals for business class flights from Worcester to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Worcester to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Worcester, Massachusetts to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $93). Flying from Worcester, Massachusetts to Caribbean Islands in October is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Worcester to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Las Vegas flights
Boston to Orlando flights
Boston to Fort Lauderdale flights
Boston to Los Angeles flights
Boston to Tampa flights
Boston to Dallas/Fort Worth flights
Boston to Miami flights
Boston to Atlanta flights
Boston to San Francisco flights
Boston to O'Hare Intl flights
Boston to Seattle flights
Boston to West Palm Beach flights
Hartford to Orlando flights
Boston to Denver flights
Boston to Sky Harbor Intl flights
Boston to Charleston flights
Boston to Fort Myers flights
Boston to Nashville flights
Boston to Reagan-National flights
Boston to New Orleans flights
Boston to Raleigh flights
Boston to Cancún flights
Boston to Dulles Intl flights
Boston to Baltimore flights
Boston to Austin flights
Boston to San Diego flights
Boston to Hobby flights
Boston to Philadelphia flights
Boston to Charlotte flights
Boston to Indianapolis flights
Boston to Savannah flights
Boston to George Bush Intcntl flights
Boston to Cincinnati flights
Boston to LaGuardia flights
Hartford to Indianapolis flights
Boston to Midway flights
Boston to Salt Lake City flights
Hartford to O'Hare Intl flights
Hartford to Tampa flights
Boston to Jacksonville flights
Boston to Detroit flights
Boston to Ontario flights
Boston to Sarasota flights
Boston to Minneapolis flights
Boston to John F Kennedy Intl flights
Boston to Portland flights
Hartford to Dallas/Fort Worth flights
Boston to Mexico City flights
Boston to Love Field flights
Hartford to Denver flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.