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$308+ Cheap flights from Worcester, MA (ORH) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$308
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$300
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($35 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 April 2025
Search Deals

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 April 30, 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 8/33:40 pmORH - NAS
2 stops19h 38mAmerican Airlines
Sat 8/96:30 pmNAS - ORH
2 stops20h 13mAmerican Airlines
Deal found 4/29$443
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 8/2010:38 amORH - NAS
1 stop6h 23mJetBlue
Sun 8/2410:05 amNAS - ORH
1 stop4h 58mJetBlue
Deal found 4/29$477

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 April 30, 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 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

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Sun 8/3

3:40 pm-11:18 am

2 stops19h 38m

Nassau Intl

Sat 8/9

6:30 pm-2:43 pm

2 stops20h 13m

$443

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Wed 8/20

10:38 am-5:01 pm

1 stop6h 23m

Nassau Intl

Sun 8/24

10:05 am-3:03 pm

1 stop4h 58m

$477

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

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 4/29

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 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 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 April 30, 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 April 30, 2025.
JetBlue
7.3
Good
2,922 reviews

Entertainment

7.3

Comfort

7.6

Crew

8.0

Overall

7.3

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

Entertainment

7.3

Comfort

7.6

Crew

8.0

Overall

7.3

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

Entertainment

7.3

Comfort

7.6

Crew

8.0

Overall

7.3

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. 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 - Castries George F. L. Charle or Worcester - Oranjestad Reina Beatrix, 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 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.

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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$689FlexibilityNo cancel feeOn-time62%

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