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$143+ Cheap flights from Worcester, MA (ORH) to Caribbean

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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Worcester to Caribbean

Cheapest flights from Worcester to Caribbean
Explore the most affordable flight options available from Worcester to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This American Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/103:30 pmORH - SJU
2 stops23h 38mAmerican Airlines
Mon 12/156:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 10/29$235
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/63:37 pmORH - SJU
2 stops20h 53mAmerican Airlines
Tue 12/96:42 pmSJU - ORH
2 stops21h 23mAmerican Airlines
Deal found 10/27$295
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/133:37 pmORH - PUJ
2 stops21h 55mAmerican Airlines
Sat 12/203:39 pmPUJ - ORH
2 stops22h 38mAmerican Airlines
Deal found 10/28$306
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/133:37 pmORH - GCM
2 stops23h 07mAmerican Airlines
Sat 12/2012:50 pmGCM - ORH
2 stops24h 27mAmerican Airlines
Deal found 10/28$315
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/113:34 pmORH - PUJ
2 stops22h 24mAmerican Airlines
Thu 12/183:39 pmPUJ - ORH
2 stops22h 43mAmerican Airlines
Deal found 10/27$318
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/23:17 pmORH - SJU
1 stop7h 35mAmerican Airlines
Fri 12/126:25 amSJU - ORH
1 stop9h 40mAmerican Airlines
Deal found 10/29$331
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:34 pmORH - SJU
1 stop7h 18mAmerican Airlines
Fri 12/268:35 pmSJU - ORH
1 stop17h 47mAmerican Airlines
Deal found 10/28$338
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/133:37 pmORH - SJU
2 stops20h 53mAmerican Airlines
Mon 12/152:36 pmSJU - ORH
2 stops25h 33mAmerican Airlines
Deal found 10/27$362
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 12/53:30 pmORH - SJU
1 stop7h 22mAmerican Airlines
Mon 12/86:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 10/27$378
This JetBlue deal was found by Cheapflights users on 10/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1811:57 amORH - SJU
1 stop7h 57mJetBlue
Fri 11/2110:55 amSJU - ORH
1 stop6h 45mJetBlue
Deal found 10/28$382
This Priceline deal was found by Cheapflights users on 10/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:02 amORH - PUJ
1 stop28h 13mJetBlue
Thu 12/1810:49 amPUJ - ORH
1 stop7h 38mJetBlue
Deal found 10/27$389
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/241:36 pmORH - NAS
2 stops21h 36mAmerican Airlines
Fri 12/2612:02 pmNAS - ORH
2 stops25h 20mAmerican Airlines
Deal found 10/27$422

Cheap flight deals from Worcester to Caribbean

Keep the following information in mind while searching for Worcester to Caribbean flight deals. Data was last updated October 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$235
(American Airlines)

One-way from

$143
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$265
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
High demand for flights, 0% potential price rise
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 October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester to Caribbean 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 October 29, 2025.
Use the filters below to find and compare flights from Worcester to Caribbean that are best for you.

Fly from

Worcester

Fly to

Caribbean

Route

Depart

Return

Price

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sat 12/13

3:37 pm-2:32 pm

2 stops21h 55m

Punta Cana

Sat 12/20

3:39 pm-1:17 pm

2 stops22h 38m

$306

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 12/13

3:37 pm-2:44 pm

2 stops23h 07m

George Town Owen Roberts Intl

Sat 12/20

12:50 pm-1:17 pm

2 stops24h 27m

$315

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Thu 12/11

3:34 pm-2:58 pm

2 stops22h 24m

Punta Cana

Thu 12/18

3:39 pm-1:22 pm

2 stops22h 43m

$318

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Tue 3/17

3:25 pm-2:50 pm

2 stops23h 25m

Punta Cana

Tue 3/31

5:15 pm-2:53 pm

2 stops21h 38m

$331

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Mon 2/16

1:44 pm-12:52 pm

2 stops22h 08m

Punta Cana

Thu 2/19

5:29 pm-1:19 pm

2 stops20h 50m

$366

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sun 2/15

1:44 pm-3:46 pm

2 stops25h 02m

Punta Cana

Thu 2/19

5:29 pm-1:19 pm

2 stops20h 50m

$380

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 3/30

11:27 am-8:20 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Thu 4/2

7:00 am-3:28 pm

1 stop8h 28m

$381

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 11/18

11:57 am-8:54 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Fri 11/21

10:55 am-4:40 pm

1 stop6h 45m

$382

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Thu 12/11

11:02 am-4:15 pm

1 stop28h 13m

Punta Cana

Thu 12/18

10:49 am-5:27 pm

1 stop7h 38m

$389

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Mon 4/6

3:25 pm-2:25 pm

2 stops23h 00m

Punta Cana

Wed 4/8

3:15 pm-2:53 pm

2 stops23h 38m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 52 results
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Best time to book a flight from Worcester to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $85). Flying from Worcester, Massachusetts to Caribbean 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 CB?

Find hourly flight availability from Worcester to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

One of the essential ways to save on airfare from Worcester, Massachusetts to Caribbean is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 71% on airfare.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated October 29, 2025.
Read reviews from past customers who have flown JetBlue from Worcester to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,907 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.2

Crew

8.0

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,907 reviews
JetBlue
7.2
Good
2,907 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.2

Crew

8.0

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

Related info for your journey

Find useful and relevant information for your journey from Worcester to Caribbean. 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?

    Located just 3.8 mi from the city center, Worcester (ORH) is the airport most travelers will use when flying to Caribbean from Worcester.

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

    Departing from Worcester, Massachusetts to Caribbean will take you 8h 53m. The distance from Worcester, Massachusetts to Caribbean is about 1681 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    While some choose either Worcester - Montego Bay Sangster Intl or Worcester - Oranjestad Reina Beatrix, Worcester - San Juan Luis Munoz Marin Intl is the most popular route from Worcester, Massachusetts to Caribbean.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Worcester to Caribbean 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?

    Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $85). Flying from Worcester, Massachusetts to Caribbean 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.

See more FAQs

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Top airline flying from Worcester to Caribbean

Discover the top airline that operate flights from Worcester to Caribbean. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$540FlexibilityNo cancel feeOn-time62%

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