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$111+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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 12/3112:19 pmORH - SJU
1 stop10h 40mAmerican Airlines
Wed 1/75:51 pmSJU - ORH
2 stops21h 02mAmerican Airlines
Deal found 12/10$388
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/3112:19 pmORH - SJU
2 stops20h 16mAmerican Airlines
Mon 1/510:03 pmSJU - ORH
2 stops16h 50mAmerican Airlines
Deal found 12/10$419
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/1511:02 amORH - SJU
1 stop9h 18mJetBlue
Thu 12/189:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/9$475
This American Airlines deal was found by Cheapflights users on 12/11. 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
Sun 12/146:25 amSJU - ORH
1 stop9h 44mAmerican Airlines
Deal found 12/11$477
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/1611:02 amORH - SJU
1 stop9h 18mJetBlue
Thu 12/189:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/9$505
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/1511:02 amORH - SJU
1 stop9h 18mJetBlue
Sun 12/219:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/9$508
This American Airlines deal was found by Cheapflights users on 12/9. 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 12/153:27 pmORH - SJU
1 stop7h 25mAmerican Airlines
Sat 12/208:35 pmSJU - ORH
1 stop17h 42mAmerican Airlines
Deal found 12/9$516
This JetBlue deal was found by Cheapflights users on 12/10. 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 12/259:34 amORH - SJU
1 stop7h 03mJetBlue
Mon 12/299:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/10$526
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/1611:02 amORH - SJU
1 stop9h 18mJetBlue
Fri 12/199:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/9$538
This JetBlue deal was found by Cheapflights users on 12/9. 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 12/1611:02 amORH - SJU
1 stop9h 18mJetBlue
Sat 12/209:36 amSJU - ORH
1 stop8h 51mJetBlue
Deal found 12/9$547
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/221:45 pmORH - AUA
2 stops26h 09mAmerican Airlines
Fri 12/265:59 pmAUA - ORH
2 stops44h 18mAmerican Airlines
Deal found 12/11$583
This American Airlines deal was found by Cheapflights users on 12/10. 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 - NAS
2 stops20h 21mAmerican Airlines
Thu 1/112:10 pmNAS - ORH
2 stops25h 07mAmerican Airlines
Deal found 12/10$591

Find flight deals from Worcester to Caribbean

Keep the following information in mind while searching for Worcester to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$227
(American Airlines)

One-way from

$111
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$388
From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($25 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 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 12, 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

Mon 1/12

2:18 pm-11:56 pm

1 stop8h 38m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:30 am-1:53 pm

1 stop8h 23m

$227

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 2/24

1:40 pm-1:00 pm

2 stops22h 20m

San Juan Luis Munoz Marin Intl

Thu 3/5

8:15 am-1:15 pm

2 stops30h 00m

$291

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Thu 2/19

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Wed 2/25

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Wed 2/18

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Wed 2/25

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Thu 2/19

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Tue 2/24

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Tue 2/17

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Wed 2/25

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Tue 2/17

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Tue 2/24

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Mon 2/23

4:30 pm-3:20 pm

2 stops21h 50m

Oranjestad Reina Beatrix

Wed 2/25

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Wed 2/18

4:30 pm-12:55 pm

2 stops19h 25m

Oranjestad Reina Beatrix

Tue 2/24

4:35 pm-3:33 pm

2 stops23h 58m

$320

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Tue 2/24

4:30 pm-12:26 pm

2 stops19h 56m

Nassau Intl

Wed 3/4

6:27 pm-3:33 pm

2 stops21h 06m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 49 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 $88). 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 December 12, 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 December 12, 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
2,899 reviews

Entertainment

7.2

Overall

7.2

Comfort

7.6

Boarding

7.4

Crew

8.0

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
2,899 reviews
JetBlue
7.2
Good
2,899 reviews

Entertainment

7.2

Overall

7.2

Comfort

7.6

Boarding

7.4

Crew

8.0

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. 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 7h. 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 - Oranjestad Reina Beatrix 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, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $88). 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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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$299FlexibilityNo cancel feeOn-time62%

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