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$124+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$289
(JetBlue)

One-way from

$124
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$205
From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 10/314:17 pmORH - SJU
1 stop7h 42mAmerican Airlines
Fri 11/76:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 9/9$291
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 12/43:34 pmORH - SJU
2 stops25h 18mAmerican Airlines
Fri 12/126:25 amSJU - ORH
1 stop9h 40mAmerican Airlines
Deal found 9/9$295
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 11/83:27 pmORH - SJU
1 stop7h 25mAmerican Airlines
Sat 11/156:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 9/9$384
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 11/113:27 pmORH - SJU
1 stop7h 25mAmerican Airlines
Wed 11/195:59 pmSJU - ORH
2 stops21h 52mAmerican Airlines
Deal found 9/9$388
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Wed 11/193:27 pmORH - SJU
2 stops23h 27mAmerican Airlines
Fri 11/286:25 amSJU - ORH
1 stop9h 26mAmerican Airlines
Deal found 9/9$395
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 12/113:34 pmORH - SJU
2 stops20h 27mAmerican Airlines
Sun 12/146:25 amSJU - ORH
1 stop9h 44mAmerican Airlines
Deal found 9/10$403
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 11/73:27 pmORH - SJU
1 stop7h 25mAmerican Airlines
Sat 11/156:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 9/9$416
This American Airlines deal was found by Cheapflights users on 9/9. 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 12/13:17 pmORH - SJU
2 stops21h 21mAmerican Airlines
Mon 12/86:42 pmSJU - ORH
2 stops21h 27mAmerican Airlines
Deal found 9/9$420
This JetBlue deal was found by Cheapflights users on 9/9. 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.
Thu 11/2712:07 pmORH - SJU
1 stop8h 22mJetBlue
Fri 12/55:05 amSJU - ORH
1 stop10h 40mJetBlue
Deal found 9/9$422
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 9/254:23 pmORH - SJU
2 stops18h 48mAmerican Airlines
Mon 9/294:43 pmSJU - ORH
2 stops23h 16mAmerican Airlines
Deal found 9/10$435
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sun 11/233:17 pmORH - SJU
2 stops18h 55mAmerican Airlines
Tue 12/25:59 pmSJU - ORH
2 stops22h 06mAmerican Airlines
Deal found 9/9$438
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sun 11/233:17 pmORH - SJU
2 stops18h 55mAmerican Airlines
Fri 11/286:25 amSJU - ORH
1 stop9h 26mAmerican Airlines
Deal found 9/9$445

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 September 11, 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

Sat 1/17

11:45 am-8:05 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Sat 1/31

6:00 am-3:55 pm

1 stop10h 55m

$289

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 2/5

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:30 am-2:53 pm

1 stop9h 23m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Wed 2/4

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:30 am-2:53 pm

1 stop9h 23m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 1/31

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Sat 2/14

6:40 am-2:53 pm

1 stop9h 13m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Fri 10/31

4:17 pm-11:59 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Thu 11/6

6:25 am-3:02 pm

1 stop9h 37m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 2/5

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:30 am-2:53 pm

1 stop9h 23m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 2/1

3:25 pm-11:40 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:30 am-2:53 pm

1 stop9h 23m

$291

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 11/24

3:17 pm-10:10 am

2 stops17h 53m

San Juan Luis Munoz Marin Intl

Wed 12/3

6:25 am-3:05 pm

1 stop9h 40m

$295

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 11/30

3:17 pm-3:46 am

1 stop11h 29m

San Juan Luis Munoz Marin Intl

Mon 12/8

6:42 pm-3:09 pm

2 stops21h 27m

$295

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 11/10

3:27 pm-11:52 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Tue 11/18

6:42 pm-3:02 pm

2 stops21h 20m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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, 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 June is currently the most expensive (average of $339). 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 September 11, 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.

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 September 11, 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
2,913 reviews

Crew

8.0

Boarding

7.4

Entertainment

7.3

Overall

7.2

Food

6.7

Comfort

7.6

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
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Crew

8.0

Boarding

7.4

Entertainment

7.3

Overall

7.2

Food

6.7

Comfort

7.6

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 7h 15m. 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 cheapest airlines to fly from Worcester, Massachusetts to Caribbean one-way?

    $124 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on JetBlue and Delta, with prices starting from $143 and $314, respectively.

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

    While some choose either Worcester - Oranjestad Reina Beatrix or Worcester - Bridgetown Grantley Adams 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 June is currently the most expensive (average of $339). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$689FlexibilityNo cancel feeOn-time62%

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