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$256+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$285
(JetBlue)

One-way from

$256
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$303
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. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 20, 2025.

This JetBlue deal was found by Cheapflights users on 2/19. 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.
Mon 3/241:47 pmORH - SJU
1 stop9h 50mJetBlue
Wed 3/266:00 amSJU - ORH
1 stop9h 22mJetBlue
Deal found 2/19$285
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/12:10 pmORH - SJU
2 stops20h 45mAmerican Airlines
Wed 4/306:04 pmSJU - ORH
2 stops19h 21mAmerican Airlines
Deal found 2/20$333
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/212:18 pmORH - NAS
2 stops21h 14mAmerican Airlines
Mon 4/286:26 pmNAS - ORH
2 stops18h 59mAmerican Airlines
Deal found 2/19$425
This American Airlines deal was found by Cheapflights users on 2/18. 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 3/202:12 pmORH - PUJ
1 stop23h 43mAmerican Airlines
Tue 3/254:50 pmPUJ - ORH
2 stops20h 50mAmerican Airlines
Deal found 2/18$447
This American Airlines deal was found by Cheapflights users on 2/20. 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 5/22:18 pmORH - AUA
2 stops25h 47mAmerican Airlines
Fri 5/94:50 pmAUA - ORH
2 stops20h 55mAmerican Airlines
Deal found 2/20$447
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/172:12 pmORH - GCM
2 stops22h 33mAmerican Airlines
Tue 3/2512:45 pmGCM - ORH
2 stops23h 55mAmerican Airlines
Deal found 2/19$580
This American Airlines deal was found by Cheapflights users on 2/19. 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 6/251:40 pmORH - SDQ
2 stops21h 20mAmerican Airlines
Wed 8/65:00 pmSDQ - ORH
2 stops20h 10mAmerican Airlines
Deal found 2/19$741
This Delta deal was found by Cheapflights users on 2/20. 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 3/174:15 pmORH - NAS
1 stop22h 33mDelta
Mon 3/245:25 pmNAS - ORH
2 stops21h 29mDelta
Deal found 2/20$791
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 2/254:00 pmORH - AUA
2 stops20h 00mDelta
Sat 3/14:35 pmAUA - ORH
2 stops23h 10mDelta
Deal found 2/20$970

Find flights from Worcester to Caribbean within your budget

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 February 20, 2025.

Fly from

Worcester

Fly to

Caribbean

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 3/24

1:47 pm-11:37 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Wed 3/26

6:00 am-3:22 pm

1 stop9h 22m

$285

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 4/1

2:10 pm-10:55 am

2 stops20h 45m

San Juan Luis Munoz Marin Intl

Wed 4/30

6:04 pm-1:25 pm

2 stops19h 21m

$333

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Mon 4/21

2:18 pm-11:32 am

2 stops21h 14m

Nassau Intl

Mon 4/28

6:26 pm-1:25 pm

2 stops18h 59m

$425

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Thu 3/20

2:12 pm-1:55 pm

1 stop23h 43m

Punta Cana

Tue 3/25

4:50 pm-1:40 pm

2 stops20h 50m

$447

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Fri 5/2

2:18 pm-4:05 pm

2 stops25h 47m

Oranjestad Reina Beatrix

Fri 5/9

4:50 pm-1:45 pm

2 stops20h 55m

$447

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 3/17

2:12 pm-11:45 am

2 stops22h 33m

George Town Owen Roberts Intl

Tue 3/25

12:45 pm-1:40 pm

2 stops23h 55m

$580

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Wed 6/25

1:40 pm-11:00 am

2 stops21h 20m

Santo Domingo Las Americas

Wed 8/6

5:00 pm-1:10 pm

2 stops20h 10m

$741

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Mon 3/17

4:15 pm-2:48 pm

1 stop22h 33m

Nassau Intl

Mon 3/24

5:25 pm-2:54 pm

2 stops21h 29m

$791

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 3/1

1:46 pm-9:44 pm

1 stop6h 58m

$256

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Fri 2/28

2:15 pm-12:15 pm

2 stops21h 00m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 11 results
1
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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.

Travel insights for flights from Worcester to Caribbean

Get recent, data-driven insights about flights from Worcester to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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 February 20, 2025.
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
7.4
Good
3,070 reviews
Delta
8.0
Very good
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,219 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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 - Oranjestad Reina Beatrix or Worcester - Nassau Intl, 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 March is currently the most expensive (average of $363). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$826FlexibilityNo cancel feeOn-time62%
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