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Caribbean Islands

$243+ Cheap flights from Worcester, MA (ORH) to Caribbean Islands

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheap flight deals from Worcester to Caribbean Islands

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

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$308
(American Airlines)

One-way from

$243
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$300
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 Islands
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One-way flight from Worcester to Caribbean Islands
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Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 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 Islands

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

This American Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 10/133:25 pmORH - SJU
2 stops19h 25mAmerican Airlines
Thu 10/166:30 amSJU - ORH
2 stops8h 23mAmerican Airlines
Deal found 4/29$308
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/163:37 pmORH - SJU
1 stop8h 42mJetBlue
Sat 5/178:45 amSJU - ORH
1 stop7h 20mJetBlue
Deal found 4/29$429
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 9/143:25 pmORH - AUA
2 stops20h 00mAmerican Airlines
Fri 9/191:00 pmAUA - ORH
2 stops25h 53mAmerican Airlines
Deal found 4/29$447
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/143:37 pmORH - PSE
1 stop8h 22mJetBlue
Sun 5/185:09 amPSE - ORH
1 stop9h 33mJetBlue
Deal found 4/29$802
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Fri 11/213:25 pmORH - STT
2 stops23h 23mAmerican Airlines
Fri 11/286:15 pmSTT - ORH
2 stops21h 38mAmerican Airlines
Deal found 4/28$1,275

Cheapflights Fare Finder

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

Fly from

Worcester

Fly to

Caribbean Islands

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Mon 10/13

3:25 pm-10:50 am

2 stops19h 25m

San Juan Luis Munoz Marin Intl

Thu 10/16

6:30 am-2:53 pm

2 stops8h 23m

$308

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Fri 5/16

3:37 pm-12:19 am

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Sat 5/17

8:45 am-4:05 pm

1 stop7h 20m

$429

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Tue 5/20

1:46 pm-1:45 pm

2 stops23h 59m

Oranjestad Reina Beatrix

Thu 5/29

5:10 pm-1:16 pm

2 stops20h 06m

$502

WorcesterPonce

ORH - PSE

ORHPSE

Worcester

Wed 5/14

3:37 pm-11:59 pm

1 stop8h 22m

Ponce Mercedita

Sun 5/18

5:09 am-2:42 pm

1 stop9h 33m

$802

WorcesterPonce

ORH - PSE

ORHPSE

Worcester

Fri 5/9

3:37 pm-11:59 pm

1 stop8h 22m

$243

WorcesterRoad Town

ORH - EIS

ORHEIS

Worcester

Sat 6/28

1:49 pm-3:51 pm

2 stops50h 02m

$521

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Best time to book a flight from Worcester to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $254). Flying from Worcester, Massachusetts to Caribbean Islands 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 EPX?

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

When flying from Worcester, Massachusetts to Caribbean Islands, 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 Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 29, 2025.
Get a feel of what it's like to fly with JetBlue and American Airlines from Worcester to Caribbean Islands by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.3
Good
2,922 reviews

Entertainment

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Crew

8.0

Overall

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
JetBlue
7.3
Good
2,922 reviews
JetBlue
7.3
Good
2,922 reviews

Entertainment

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Crew

8.0

Overall

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,922 reviews

Entertainment

7.3

Boarding

7.5

Comfort

7.6

Food

6.7

Crew

8.0

Overall

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job

Related info for your journey

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

    Worcester (ORH), located 3.8 mi from the city center, is the airport you fly out of when you book flights from Worcester to Caribbean Islands.

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

    The most popular route from Worcester, Massachusetts to Caribbean Islands is Worcester - San Juan Luis Munoz Marin Intl. You may also consider Worcester - Castries George F. L. Charle or Worcester - Oranjestad Reina Beatrix.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Worcester to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $254). Flying from Worcester, Massachusetts to Caribbean Islands 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.

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Top airline flying from Worcester to Caribbean Islands

Discover the top airline that operate flights from Worcester to Caribbean Islands. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$689FlexibilityNo cancel feeOn-time62%

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