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Caribbean Islands

$103+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$421
(American Airlines)

One-way from

$103
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$238
From Worcester to Caribbean Islands
Search Deals
One-way flight from Worcester to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 1, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 11/233:29 pmORH - SJU
1 stop7h 18mAmerican Airlines
Sat 11/296:25 amSJU - ORH
1 stop9h 39mAmerican Airlines
Deal found 7/30$421
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/173:59 pmORH - SDQ
1 stop9h 16mJetBlue
Sun 8/246:05 amSDQ - ORH
1 stop8h 58mJetBlue
Deal found 7/31$434
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/173:59 pmORH - PUJ
1 stop17h 41mJetBlue
Sat 8/2310:35 amPUJ - ORH
1 stop28h 28mJetBlue
Deal found 7/30$442
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/134:24 pmORH - MBJ
2 stops19h 06mAmerican Airlines
Sat 9/202:38 pmMBJ - ORH
2 stops24h 20mAmerican Airlines
Deal found 7/30$460
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/273:20 pmORH - PUJ
2 stops22h 55mAmerican Airlines
Wed 9/34:25 pmPUJ - ORH
2 stops23h 34mAmerican Airlines
Deal found 7/30$471
This JetBlue deal was found by Cheapflights users on 7/31. 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 8/810:45 amORH - SJU
1 stop9h 49mJetBlue
Thu 8/146:45 amSJU - ORH
1 stop8h 18mJetBlue
Deal found 7/31$493
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/293:20 pmORH - GCM
2 stops45h 05mAmerican Airlines
Fri 9/512:10 pmGCM - ORH
2 stops26h 48mAmerican Airlines
Deal found 7/31$504
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/173:20 pmORH - SDQ
2 stops18h 05mAmerican Airlines
Sun 8/247:20 pmSDQ - ORH
2 stops19h 35mAmerican Airlines
Deal found 7/31$516
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/204:24 pmORH - STT
2 stops20h 26mAmerican Airlines
Sat 9/274:05 pmSTT - ORH
2 stops23h 53mAmerican Airlines
Deal found 7/31$529
This American Airlines deal was found by Cheapflights users on 8/1. 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 8/113:20 pmORH - AUA
1 stop22h 10mAmerican Airlines
Thu 8/145:05 pmAUA - ORH
2 stops21h 50mAmerican Airlines
Deal found 8/1$536
This American Airlines deal was found by Cheapflights users on 7/31. 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 12/243:25 pmORH - NAS
2 stops20h 05mAmerican Airlines
Tue 12/302:10 pmNAS - ORH
1 stop24h 43mAmerican Airlines
Deal found 7/31$539
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:30 pmORH - MBJ
1 stop22h 35mJetBlue
Sat 9/2011:30 amMBJ - ORH
1 stop27h 20mJetBlue
Deal found 7/30$542

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 August 1, 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

Sun 11/23

3:29 pm-11:47 pm

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Sat 11/29

6:25 am-3:04 pm

1 stop9h 39m

$421

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Sun 8/17

3:59 pm-1:15 am

1 stop9h 16m

Santo Domingo Las Americas

Sun 8/24

6:05 am-3:03 pm

1 stop8h 58m

$434

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Sun 8/17

3:59 pm-9:40 am

1 stop17h 41m

Punta Cana

Sat 8/23

10:35 am-3:03 pm

1 stop28h 28m

$442

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

Sat 9/13

4:24 pm-10:30 am

2 stops19h 06m

Montego Bay Sangster Intl

Sat 9/20

2:38 pm-3:58 pm

2 stops24h 20m

$460

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Wed 8/27

3:20 pm-2:15 pm

2 stops22h 55m

Punta Cana

Wed 9/3

4:25 pm-3:59 pm

2 stops23h 34m

$471

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Fri 8/29

3:20 pm-11:25 am

2 stops45h 05m

George Town Owen Roberts Intl

Fri 9/5

12:10 pm-3:58 pm

2 stops26h 48m

$504

WorcesterSanto Domingo

ORH - SDQ

ORHSDQ

Worcester

Sun 8/17

3:20 pm-9:25 am

2 stops18h 05m

Santo Domingo Las Americas

Sun 8/24

7:20 pm-2:55 pm

2 stops19h 35m

$516

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Fri 12/5

11:57 am-9:20 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Sat 12/13

5:05 am-2:45 pm

1 stop10h 40m

$524

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

Sat 9/20

4:24 pm-12:50 pm

2 stops20h 26m

Saint Thomas Island Cyril E King

Sat 9/27

4:05 pm-3:58 pm

2 stops23h 53m

$529

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Mon 8/11

3:20 pm-1:30 pm

1 stop22h 10m

Oranjestad Reina Beatrix

Thu 8/14

5:05 pm-2:55 pm

2 stops21h 50m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 19 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 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 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 August 1, 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.

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 August 1, 2025.
See what other customers who have flown with JetBlue and American Airlines from Worcester to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.3
Good
2,914 reviews

Overall

7.3

Comfort

7.6

Boarding

7.4

Crew

8.0

Food

6.7

Entertainment

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
JetBlue
7.3
Good
2,914 reviews
JetBlue
7.3
Good
2,914 reviews

Overall

7.3

Comfort

7.6

Boarding

7.4

Crew

8.0

Food

6.7

Entertainment

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,914 reviews

Overall

7.3

Comfort

7.6

Boarding

7.4

Crew

8.0

Food

6.7

Entertainment

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.

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 - Punta Cana or Worcester - Castries George F. L. Charle.

  • 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 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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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$689FlexibilityNo cancel feeOn-time62%

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