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$154+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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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 April 17, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$365
(JetBlue)

One-way from

$154
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$298
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 17, 2025.

This JetBlue deal was found by Cheapflights users on 4/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/153:37 pmORH - SJU
1 stop8h 42mJetBlue
Fri 5/308:45 amSJU - ORH
1 stop7h 20mJetBlue
Deal found 4/17$365
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/151:46 pmORH - SJU
2 stops21h 13mAmerican Airlines
Fri 5/305:30 pmSJU - ORH
2 stops20h 15mAmerican Airlines
Deal found 4/17$395
This American Airlines deal was found by Cheapflights users on 4/16. 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 12/62:24 pmORH - MBJ
2 stops19h 46mAmerican Airlines
Sat 12/135:30 pmMBJ - ORH
2 stops20h 22mAmerican Airlines
Deal found 4/16$445
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/312:16 pmORH - SDQ
2 stops20h 59mAmerican Airlines
Sat 6/72:35 pmSDQ - ORH
2 stops22h 17mAmerican Airlines
Deal found 4/16$445
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Fri 5/91:46 pmORH - PUJ
2 stops23h 49mAmerican Airlines
Wed 5/144:53 pmPUJ - ORH
1 stop20h 23mAmerican Airlines
Deal found 4/16$447
This American Airlines deal was found by Cheapflights users on 4/16. 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 9/21:40 pmORH - AUA
2 stops21h 45mAmerican Airlines
Sat 9/64:45 pmAUA - ORH
2 stops20h 27mAmerican Airlines
Deal found 4/16$472
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Mon 8/41:33 pmORH - STX
2 stops26h 53mAmerican Airlines
Fri 8/151:55 pmSTX - ORH
2 stops23h 15mAmerican Airlines
Deal found 4/17$525
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Mon 8/111:40 pmORH - STT
2 stops23h 00mAmerican Airlines
Wed 8/205:25 pmSTT - ORH
2 stops19h 45mAmerican Airlines
Deal found 4/16$529
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/312:16 pmORH - SXM
2 stops24h 08mAmerican Airlines
Sat 6/74:05 pmSXM - ORH
2 stops20h 47mAmerican Airlines
Deal found 4/16$567
This JetBlue deal was found by Cheapflights users on 4/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/313:37 pmORH - SDQ
1 stop9h 58mJetBlue
Sat 6/77:07 amSDQ - ORH
1 stop7h 40mJetBlue
Deal found 4/16$610
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Mon 12/292:42 pmORH - BGI
2 stops22h 58mAmerican Airlines
Mon 1/54:55 pmBGI - ORH
2 stops22h 06mAmerican Airlines
Deal found 4/16$871
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/284:00 pmORH - PUJ
2 stops19h 30mDelta
Sat 5/33:55 pmPUJ - ORH
2 stops23h 11mDelta
Deal found 4/16$1,012

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 April 17, 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

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 5/15

3:37 pm-12:19 am

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Fri 5/30

8:45 am-4:05 pm

1 stop7h 20m

$365

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 5/15

1:46 pm-10:59 am

2 stops21h 13m

San Juan Luis Munoz Marin Intl

Fri 5/30

5:30 pm-1:45 pm

2 stops20h 15m

$395

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Sat 5/31

2:16 pm-11:15 am

2 stops20h 59m

Santo Domingo Las Americas

Sat 6/7

2:35 pm-12:52 pm

2 stops22h 17m

$445

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Fri 5/9

1:46 pm-1:35 pm

2 stops23h 49m

Punta Cana

Wed 5/14

4:53 pm-1:16 pm

1 stop20h 23m

$447

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Tue 4/29

2:18 pm-9:54 am

1 stop20h 36m

Montego Bay Sangster Intl

Sat 5/3

10:55 am-1:25 pm

1 stop25h 30m

$464

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Tue 9/2

1:40 pm-11:25 am

2 stops21h 45m

Oranjestad Reina Beatrix

Sat 9/6

4:45 pm-1:12 pm

2 stops20h 27m

$472

WorcesterChristiansted

ORH - STX

ORHSTX

Worcester

Mon 8/4

1:33 pm-4:26 pm

2 stops26h 53m

Christiansted Henry Rohlsen

Fri 8/15

1:55 pm-1:10 pm

2 stops23h 15m

$525

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

Mon 8/11

1:40 pm-12:40 pm

2 stops23h 00m

Saint Thomas Island Cyril E King

Thu 8/21

5:25 pm-1:10 pm

2 stops19h 45m

$529

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Sat 5/31

2:16 pm-2:24 pm

2 stops24h 08m

Simpson Bay Princess Juliana

Sat 6/7

4:05 pm-12:52 pm

2 stops20h 47m

$567

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Sat 5/31

3:37 pm-1:35 am

1 stop9h 58m

Santo Domingo Las Americas

Sat 6/7

7:07 am-2:47 pm

1 stop7h 40m

$610

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 18 results
1
2

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, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $254). Flying from Worcester, Massachusetts to Caribbean in December is currently the most expensive (average of $336). 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 April 17, 2025.

When flying from Worcester, Massachusetts to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 17, 2025.
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,926 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,916 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    While some choose either Worcester - Castries George F. L. Charle or Worcester - Punta Cana, 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, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $254). Flying from Worcester, Massachusetts to Caribbean in December is currently the most expensive (average of $336). 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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Alternative routes for Worcester to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$689FlexibilityNo cancel feeOn-time62%

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