HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$142+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Worcester to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 4, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$311
(JetBlue)

One-way from

$142
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$298
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 Islands
Search Deals
One-way flight from Worcester to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($36 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 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 4, 2025.

This JetBlue deal was found by Cheapflights users on 4/4. 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 8/53:59 pmORH - SJU
1 stop7h 02mJetBlue
Fri 8/156:45 amSJU - ORH
1 stop8h 18mJetBlue
Deal found 4/4$311
This American Airlines deal was found by Cheapflights users on 4/3. 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 5/31:38 pmORH - SJU
2 stops15h 22mAmerican Airlines
Tue 5/65:30 pmSJU - ORH
2 stops19h 46mAmerican Airlines
Deal found 4/3$339
This American Airlines deal was found by Cheapflights users on 4/4. 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 5/61:46 pmORH - AUA
2 stops26h 24mAmerican Airlines
Fri 5/94:50 pmAUA - ORH
2 stops20h 55mAmerican Airlines
Deal found 4/4$434
This American Airlines deal was found by Cheapflights users on 4/3. 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 9/191:42 pmORH - PUJ
2 stops22h 58mAmerican Airlines
Tue 9/234:52 pmPUJ - ORH
2 stops20h 20mAmerican Airlines
Deal found 4/3$468
This American Airlines deal was found by Cheapflights users on 4/4. 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 4/51:38 pmORH - MBJ
1 stop21h 16mAmerican Airlines
Fri 5/212:55 pmMBJ - ORH
2 stops23h 13mAmerican Airlines
Deal found 4/4$528
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/242:18 pmORH - NAS
2 stops27h 28mAmerican Airlines
Sun 4/2710:07 amNAS - ORH
2 stops27h 18mAmerican Airlines
Deal found 4/2$636
This American Airlines deal was found by Cheapflights users on 4/3. 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 4/182:18 pmORH - STX
2 stops22h 56mAmerican Airlines
Tue 4/224:55 pmSTX - ORH
2 stops20h 30mAmerican Airlines
Deal found 4/3$747

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 4, 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

Tue 8/5

3:59 pm-11:01 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Tue 8/12

6:45 am-3:03 pm

1 stop8h 18m

$311

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 5/3

1:38 pm-5:00 am

2 stops15h 22m

San Juan Luis Munoz Marin Intl

Tue 5/6

5:30 pm-1:16 pm

2 stops19h 46m

$339

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Tue 5/6

1:46 pm-4:10 pm

2 stops26h 24m

Oranjestad Reina Beatrix

Fri 5/9

4:50 pm-1:45 pm

2 stops20h 55m

$434

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Fri 9/19

1:42 pm-12:40 pm

2 stops22h 58m

Punta Cana

Tue 9/23

4:52 pm-1:12 pm

2 stops20h 20m

$468

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Thu 4/24

2:18 pm-5:46 pm

2 stops27h 28m

Nassau Intl

Sun 4/27

10:07 am-1:25 pm

2 stops27h 18m

$636

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Sun 4/20

2:18 pm-9:45 am

2 stops20h 27m

Montego Bay Sangster Intl

Sun 4/27

10:55 am-1:25 pm

1 stop25h 30m

$688

WorcesterChristiansted

ORH - STX

ORHSTX

Worcester

Fri 4/18

2:18 pm-1:14 pm

2 stops22h 56m

Christiansted Henry Rohlsen

Tue 4/22

4:55 pm-1:25 pm

2 stops20h 30m

$747

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 4/26

1:38 pm-5:00 am

2 stops15h 22m

$142

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Mon 4/21

2:18 pm-1:40 pm

2 stops23h 22m

$177

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sat 6/21

1:49 pm-10:50 am

1 stop21h 01m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 12 results
1
2

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 4, 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 4, 2025.
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,900 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
JetBlue
7.3
Good
2,920 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,900 reviews

Overall

8.0

Food

7.3

Comfort

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 cheapest airlines to fly from Worcester, Massachusetts to Caribbean Islands one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $142. However, be on the lookout for offers from JetBlue and Delta, as they are both options that can get you from Worcester, Massachusetts to Caribbean Islands for a low price.

  • 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 - Punta Cana.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Worcester to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Los Angeles flights
Boston to Las Vegas flights
Boston to O'Hare Intl flights
Boston to Orlando flights
Boston to Miami flights
Boston to Dulles Intl flights
Boston to Fort Lauderdale flights
Boston to Dallas/Fort Worth flights
Boston to Seattle flights
Boston to Tampa flights
Boston to Reagan-National flights
Boston to Baltimore flights
Hartford to Orlando flights
Boston to San Francisco flights
Boston to Nashville flights
Boston to Philadelphia flights
Boston to Newark flights
Boston to LaGuardia flights
Boston to West Palm Beach flights
Boston to Austin flights
Boston to Sky Harbor Intl flights
Boston to Cancún flights
Boston to Raleigh flights
Boston to Denver flights
Boston to Hobby flights
Boston to Atlanta flights
Boston to Charleston flights
Boston to Salt Lake City flights
Boston to San Diego flights
Boston to Charlotte flights
Boston to Fort Myers flights
Boston to Minneapolis flights
Boston to New Orleans flights
Boston to George Bush Intcntl flights
Boston to Midway flights
Hartford to O'Hare Intl flights
Hartford to Tampa flights
Boston to Pittsburgh flights
Boston to Ontario flights
Boston to John F Kennedy Intl flights
Boston to Sarasota flights
Boston to Pearson Intl flights
Boston to Savannah flights
Hartford to Las Vegas flights
Hartford to Atlanta flights
Boston to Cincinnati flights
Boston to Detroit flights
Hartford to Denver flights
Boston to Mexico City flights
Hartford to Miami flights

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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$826FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.