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Caribbean Islands

$250+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 25, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$416
(JetBlue)

One-way from

$250
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$299
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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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. 12% potential increase in price ($36 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 25, 2025.

This JetBlue deal was found by Cheapflights users on 4/25. 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 stop7h 48mJetBlue
Tue 5/208:45 amSJU - ORH
1 stop7h 20mJetBlue
Deal found 4/25$416
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/102:16 pmORH - STX
2 stops23h 38mAmerican Airlines
Wed 5/144:55 pmSTX - ORH
2 stops20h 21mAmerican Airlines
Deal found 4/25$497
This American Airlines deal was found by Cheapflights users on 4/25. 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 9/13:25 pmORH - AUA
1 stop21h 32mAmerican Airlines
Sat 9/63:30 pmAUA - ORH
2 stops23h 23mAmerican Airlines
Deal found 4/25$511
This American Airlines deal was found by Cheapflights users on 4/24. 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 7/31:49 pmORH - SJU
2 stops21h 16mAmerican Airlines
Wed 7/98:30 amSJU - ORH
1 stop6h 23mAmerican Airlines
Deal found 4/24$515

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 25, 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

Fri 5/16

3:37 pm-11:25 pm

1 stop7h 48m

San Juan Luis Munoz Marin Intl

Tue 5/20

8:45 am-4:05 pm

1 stop7h 20m

$416

WorcesterChristiansted

ORH - STX

ORHSTX

Worcester

Sat 5/10

2:16 pm-1:54 pm

2 stops23h 38m

Christiansted Henry Rohlsen

Wed 5/14

4:55 pm-1:16 pm

2 stops20h 21m

$497

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Mon 9/1

3:25 pm-12:57 pm

1 stop21h 32m

Oranjestad Reina Beatrix

Sat 9/6

3:30 pm-2:53 pm

2 stops23h 23m

$511

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Thu 7/3

1:49 pm-11:05 am

2 stops21h 16m

San Juan Luis Munoz Marin Intl

Wed 7/9

8:30 am-2:53 pm

1 stop6h 23m

$515

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 8/5

3:59 pm-11:01 pm

1 stop7h 02m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

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 25, 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 25, 2025.
JetBlue
7.3
Good
2,922 reviews

Comfort

7.6

Overall

7.3

Entertainment

7.3

Crew

8.0

Boarding

7.5

Food

6.7

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

Comfort

7.6

Overall

7.3

Entertainment

7.3

Crew

8.0

Boarding

7.5

Food

6.7

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

Comfort

7.6

Overall

7.3

Entertainment

7.3

Crew

8.0

Boarding

7.5

Food

6.7

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 - Christiansted Henry Rohlsen.

  • 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$689FlexibilityNo cancel feeOn-time62%

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