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$219+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$355
(American Airlines)

One-way from

$219
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$264
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
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One-way flight from Worcester to Caribbean
Search Deals
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 March 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 March 28, 2025.

This American Airlines deal was found by Cheapflights users on 3/27. 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 5/71:46 pmORH - SJU
2 stops15h 26mAmerican Airlines
Sun 5/115:30 pmSJU - ORH
2 stops19h 46mAmerican Airlines
Deal found 3/27$355
This JetBlue deal was found by Cheapflights users on 3/27. 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 4/812:05 pmORH - SJU
1 stop8h 19mJetBlue
Wed 4/164:30 amSJU - ORH
1 stop9h 40mJetBlue
Deal found 3/27$428
This American Airlines deal was found by Cheapflights users on 3/26. 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 5/111:46 pmORH - PUJ
1 stop20h 58mAmerican Airlines
Sun 5/184:53 pmPUJ - ORH
1 stop20h 23mAmerican Airlines
Deal found 3/26$453
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/212:18 pmORH - MBJ
2 stops20h 27mAmerican Airlines
Fri 4/254:00 pmMBJ - ORH
2 stops44h 25mAmerican Airlines
Deal found 3/27$479
This American Airlines deal was found by Cheapflights users on 3/27. 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 5/121:46 pmORH - GCM
2 stops22h 24mAmerican Airlines
Mon 5/1912:25 pmGCM - ORH
2 stops23h 51mAmerican Airlines
Deal found 3/27$486
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/12:10 pmORH - AUA
2 stops21h 20mAmerican Airlines
Thu 4/104:50 pmAUA - ORH
2 stops20h 35mAmerican Airlines
Deal found 3/27$522
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/34:00 pmORH - PUJ
2 stops22h 37mDelta
Wed 11/125:23 pmPUJ - ORH
2 stops22h 49mDelta
Deal found 3/27$932

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 March 28, 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

Wed 5/7

1:46 pm-5:12 am

2 stops15h 26m

San Juan Luis Munoz Marin Intl

Sun 5/11

5:30 pm-1:16 pm

2 stops19h 46m

$355

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 4/8

12:05 pm-8:24 pm

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Wed 4/16

4:30 am-2:10 pm

1 stop9h 40m

$428

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sun 5/11

1:46 pm-10:44 am

1 stop20h 58m

Punta Cana

Sun 5/18

4:53 pm-1:16 pm

1 stop20h 23m

$453

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Mon 4/21

2:18 pm-9:45 am

2 stops20h 27m

Montego Bay Sangster Intl

Fri 4/25

4:00 pm-1:25 pm

2 stops44h 25m

$479

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 5/12

1:46 pm-11:10 am

2 stops22h 24m

George Town Owen Roberts Intl

Mon 5/19

12:25 pm-1:16 pm

2 stops23h 51m

$486

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 4/5

1:38 pm-10:59 am

2 stops21h 21m

$219

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 4/5

1:32 pm-11:19 pm

1 stop9h 47m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March 28, 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 March 28, 2025.
JetBlue
7.3
Good
2,923 reviews

Boarding

7.5

Comfort

7.6

Food

6.7

Entertainment

7.3

Overall

7.3

Crew

8.0

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
2,923 reviews
JetBlue
7.3
Good
2,923 reviews

Boarding

7.5

Comfort

7.6

Food

6.7

Entertainment

7.3

Overall

7.3

Crew

8.0

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
2,923 reviews

Boarding

7.5

Comfort

7.6

Food

6.7

Entertainment

7.3

Overall

7.3

Crew

8.0

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 - 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, 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$826FlexibilityNo cancel feeOn-time62%
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