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Caribbean Islands

$111+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Thu 12/254:30 pmGCM - ORH
2 stops44h 52mAmerican Airlines
Deal found 12/17$420
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Fri 12/261:05 pmGCM - ORH
2 stops24h 17mAmerican Airlines
Deal found 12/17$422
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Mon 12/293:45 pmGCM - ORH
2 stops21h 32mAmerican Airlines
Deal found 12/17$431
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/181:45 pmORH - SJU
1 stop9h 14mAmerican Airlines
Thu 12/258:35 pmSJU - ORH
1 stop17h 42mAmerican Airlines
Deal found 12/16$444
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/231:45 pmORH - AUA
2 stops25h 05mAmerican Airlines
Tue 12/305:59 pmAUA - ORH
2 stops18h 55mAmerican Airlines
Deal found 12/16$447
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Sun 12/283:35 pmGCM - ORH
2 stops45h 42mAmerican Airlines
Deal found 12/17$450
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/181:45 pmORH - SJU
1 stop9h 14mAmerican Airlines
Sat 12/208:35 pmSJU - ORH
1 stop17h 42mAmerican Airlines
Deal found 12/17$477
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Thu 1/13:35 pmGCM - ORH
2 stops21h 42mAmerican Airlines
Deal found 12/17$506
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/201:45 pmORH - GCM
2 stops25h 40mAmerican Airlines
Mon 12/294:30 pmGCM - ORH
2 stops20h 47mAmerican Airlines
Deal found 12/15$510
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/201:45 pmORH - SJU
2 stops22h 56mAmerican Airlines
Wed 12/313:49 pmSJU - ORH
2 stops22h 33mAmerican Airlines
Deal found 12/16$520
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Fri 1/27:30 amGCM - ORH
2 stops29h 47mAmerican Airlines
Deal found 12/17$527
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/231:45 pmORH - PUJ
2 stops44h 43mAmerican Airlines
Tue 12/304:45 pmPUJ - ORH
2 stops20h 09mAmerican Airlines
Deal found 12/15$563

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 December 18, 2025.

Round-trip from

$231
(American Airlines)

One-way from

$111
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$386
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. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 18, 2025.
Use the filters below to find and compare flights from Worcester to Caribbean Islands that are best for you.

Fly from

Worcester

Fly to

Caribbean Islands

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 3/15

1:44 pm-10:40 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Thu 3/19

11:32 am-1:18 pm

2 stops25h 46m

$231

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 1/29

2:18 pm-11:56 pm

1 stop8h 38m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:00 am-1:53 pm

1 stop7h 53m

$290

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 1/5

1:45 pm-11:59 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

Thu 1/8

2:31 pm-1:53 pm

2 stops24h 22m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 2/17

1:40 pm-10:07 am

2 stops19h 27m

San Juan Luis Munoz Marin Intl

Mon 2/23

4:03 pm-1:15 pm

2 stops22h 12m

$293

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 1/5

1:45 pm-11:59 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

Wed 1/7

1:24 pm-1:53 pm

2 stops25h 29m

$293

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Sat 4/25

4:26 pm-1:10 pm

2 stops20h 44m

Oranjestad Reina Beatrix

Sat 5/2

5:00 pm-2:53 pm

1 stop21h 53m

$306

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Tue 3/17

1:44 pm-10:57 am

1 stop21h 13m

Punta Cana

Tue 3/31

1:46 pm-1:18 pm

1 stop23h 32m

$309

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Sat 5/16

4:26 pm-1:10 pm

2 stops20h 44m

Oranjestad Reina Beatrix

Sat 5/23

4:50 pm-2:53 pm

2 stops22h 03m

$318

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Sat 5/9

4:26 pm-12:55 pm

1 stop20h 29m

Oranjestad Reina Beatrix

Sat 5/16

4:50 pm-2:53 pm

2 stops22h 03m

$319

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Sat 1/31

2:23 pm-1:34 pm

2 stops23h 11m

Montego Bay Sangster Intl

Sat 2/7

4:22 pm-1:53 pm

2 stops21h 31m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
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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 $88). Flying from Worcester, Massachusetts to Caribbean Islands in September is currently the most expensive (average of $147). 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.

What is the cheapest time of day to fly from ORH to EPX?

Find hourly flight availability from Worcester to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Worcester, Massachusetts to Caribbean Islands in the evening. If you’re flexible enough to do this you can expect to save up to 71% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated December 18, 2025.
See what other customers who have flown with JetBlue from Worcester to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,897 reviews

Comfort

7.6

Entertainment

7.2

Boarding

7.4

Crew

8.0

Overall

7.2

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Samuel,Nov 2025

PBI - HPN

Incessant announcements hawking the JB Card, other items to purchase, seat back tables up 45 minutes before we landed....more announcements....Give your customer a break!
JetBlue
7.2
Good
2,897 reviews
JetBlue
7.2
Good
2,897 reviews

Comfort

7.6

Entertainment

7.2

Boarding

7.4

Crew

8.0

Overall

7.2

Food

6.7

Reviews

1 / 20
2.0
Mediocre

Samuel,Nov 2025

PBI - HPN

Incessant announcements hawking the JB Card, other items to purchase, seat back tables up 45 minutes before we landed....more announcements....Give your customer a break!

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 8h 56m. 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 - Punta Cana or Worcester - Oranjestad Reina Beatrix.

  • 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 $88). Flying from Worcester, Massachusetts to Caribbean Islands in September is currently the most expensive (average of $147). 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.

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Top airline flying from Worcester to Caribbean Islands

Discover the top airline that operate flights from Worcester to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$99Average$299FlexibilityNo cancel feeOn-time62%

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