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$143+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$362
(American Airlines)

One-way from

$143
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$303
From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($29 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 June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. 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 11/163:25 pmORH - SJU
1 stop7h 06mAmerican Airlines
Sun 11/236:30 amSJU - ORH
1 stop9h 23mAmerican Airlines
Deal found 6/10$362
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/53:29 pmORH - NAS
2 stops18h 36mAmerican Airlines
Thu 7/106:35 pmNAS - ORH
2 stops20h 29mAmerican Airlines
Deal found 6/10$387
This JetBlue deal was found by Cheapflights users on 6/10. 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 7/13:59 pmORH - SJU
1 stop7h 00mJetBlue
Tue 7/157:00 amSJU - ORH
1 stop8h 03mJetBlue
Deal found 6/10$391
This American Airlines deal was found by Cheapflights users on 6/10. 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 11/23:25 pmORH - AUA
2 stops19h 50mAmerican Airlines
Thu 11/65:55 pmAUA - ORH
2 stops21h 58mAmerican Airlines
Deal found 6/10$398
This deal was found by Cheapflights users on 6/12. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/510:38 amORH - NAS
1 stop6h 30mJetBlue
Thu 7/109:45 amNAS - ORH
1 stop5h 18mJetBlue
Deal found 6/12$411
This JetBlue deal was found by Cheapflights users on 6/11. 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 7/161:34 pmORH - SDQ
1 stop12h 18mJetBlue
Tue 7/226:05 amSDQ - ORH
1 stop8h 58mJetBlue
Deal found 6/11$454
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/253:29 pmORH - MBJ
2 stops24h 31mAmerican Airlines
Sat 8/21:35 pmMBJ - ORH
2 stops24h 29mAmerican Airlines
Deal found 6/10$470
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/263:29 pmORH - GCM
2 stops20h 53mAmerican Airlines
Sat 8/23:05 pmGCM - ORH
2 stops22h 59mAmerican Airlines
Deal found 6/11$529
This American Airlines deal was found by Cheapflights users on 6/10. 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 6/231:49 pmORH - PUJ
1 stop20h 55mAmerican Airlines
Sun 6/2911:44 amPUJ - ORH
1 stop25h 08mAmerican Airlines
Deal found 6/10$532
This American Airlines deal was found by Cheapflights users on 6/11. 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 7/163:29 pmORH - SDQ
2 stops53h 26mAmerican Airlines
Tue 7/227:20 pmSDQ - ORH
2 stops19h 44mAmerican Airlines
Deal found 6/11$555
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/133:20 pmORH - PLS
2 stops19h 30mAmerican Airlines
Mon 8/183:35 pmPLS - ORH
2 stops23h 20mAmerican Airlines
Deal found 6/11$636
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 8/153:55 pmORH - PLS
2 stops20h 40mDelta
Tue 8/192:00 pmPLS - ORH
2 stops24h 56mDelta
Deal found 6/11$1,140

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 June 12, 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

Sun 11/16

3:25 pm-11:31 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Sun 11/23

6:30 am-2:53 pm

1 stop9h 23m

$362

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Sat 7/5

3:29 pm-10:05 am

2 stops18h 36m

Nassau Intl

Thu 7/10

6:35 pm-3:04 pm

2 stops20h 29m

$387

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Tue 7/1

3:59 pm-10:59 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Tue 7/15

7:00 am-3:03 pm

1 stop8h 03m

$391

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Sun 11/2

3:25 pm-12:15 pm

2 stops19h 50m

Oranjestad Reina Beatrix

Thu 11/6

5:55 pm-2:53 pm

2 stops21h 58m

$398

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

Sat 7/5

10:38 am-5:08 pm

1 stop6h 30m

Nassau Intl

Thu 7/10

9:45 am-3:03 pm

1 stop5h 18m

$411

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Wed 7/16

1:34 pm-1:52 am

1 stop12h 18m

Santo Domingo Las Americas

Tue 7/22

6:05 am-3:03 pm

1 stop8h 58m

$454

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Fri 7/25

3:29 pm-3:00 pm

2 stops24h 31m

Montego Bay Sangster Intl

Sat 8/2

1:35 pm-3:04 pm

2 stops24h 29m

$470

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 7/26

3:29 pm-11:22 am

2 stops20h 53m

George Town Owen Roberts Intl

Sat 8/2

3:05 pm-3:04 pm

2 stops22h 59m

$529

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Mon 6/23

1:49 pm-10:44 am

1 stop20h 55m

Punta Cana

Sun 6/29

11:44 am-12:52 pm

1 stop25h 08m

$532

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Wed 7/16

3:29 pm-8:55 pm

2 stops53h 26m

Santo Domingo Las Americas

Tue 7/22

7:20 pm-3:04 pm

2 stops19h 44m

$555

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 17 results
1
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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 June is currently the most expensive (average of $339). 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 June 12, 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 June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,925 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,946 reviews

Crew

8.5

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 - Santo Domingo Las Americas, 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 June is currently the most expensive (average of $339). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$223Average$689FlexibilityNo cancel feeOn-time62%

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