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Caribbean Islands

$148+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$235
(American Airlines)

One-way from

$148
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$285
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 Islands
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One-way flight from Worcester to Caribbean Islands
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/103:30 pmORH - SJU
1 stop7h 22mAmerican Airlines
Mon 12/156:25 amSJU - ORH
1 stop9h 37mAmerican Airlines
Deal found 11/1$294
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 12/301:45 pmORH - NAS
2 stops22h 27mAmerican Airlines
Tue 1/62:58 pmNAS - ORH
2 stops22h 55mAmerican Airlines
Deal found 11/2$409
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 12/291:45 pmORH - NAS
1 stop22h 01mAmerican Airlines
Tue 1/610:47 amNAS - ORH
2 stops27h 06mAmerican Airlines
Deal found 11/2$412
This JetBlue deal was found by Cheapflights users on 11/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1511:57 amORH - SJU
1 stop7h 57mJetBlue
Sat 11/226:45 amSJU - ORH
1 stop9h 36mJetBlue
Deal found 11/1$426
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 11/173:27 pmORH - SJU
1 stop7h 25mAmerican Airlines
Fri 11/216:25 amSJU - ORH
1 stop9h 26mAmerican Airlines
Deal found 11/2$431
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/113:34 pmORH - SJU
1 stop7h 18mAmerican Airlines
Sun 12/146:25 amSJU - ORH
1 stop9h 44mAmerican Airlines
Deal found 11/2$434
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sat 11/153:27 pmORH - SJU
2 stops20h 46mAmerican Airlines
Sat 11/226:25 amSJU - ORH
1 stop9h 26mAmerican Airlines
Deal found 11/1$435
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/103:30 pmORH - SDQ
2 stops24h 53mAmerican Airlines
Thu 12/186:57 pmSDQ - ORH
2 stops19h 25mAmerican Airlines
Deal found 11/1$437
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:02 amORH - SDQ
1 stop20h 32mJetBlue
Thu 12/188:15 pmSDQ - ORH
1 stop13h 32mJetBlue
Deal found 11/1$464
This SmartFares deal was found by Cheapflights users on 11/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:57 amORH - SDQ
1 stop19h 37mJetBlue
Sun 11/234:09 amSDQ - ORH
1 stop11h 59mJetBlue
Deal found 11/1$466
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 11/233:17 pmORH - NAS
2 stops20h 54mAmerican Airlines
Thu 11/2712:00 pmNAS - ORH
1 stop26h 51mAmerican Airlines
Deal found 11/1$478
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/63:27 pmORH - AUA
2 stops23h 56mAmerican Airlines
Sat 11/85:54 pmAUA - ORH
1 stop22h 08mAmerican Airlines
Deal found 11/2$480

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 November 3, 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

Thu 1/29

2:18 pm-11:56 pm

1 stop8h 38m

San Juan Luis Munoz Marin Intl

Mon 2/2

4:49 pm-1:53 pm

2 stops22h 04m

$235

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Wed 12/10

3:30 pm-11:52 pm

1 stop7h 22m

San Juan Luis Munoz Marin Intl

Mon 12/15

6:25 am-3:02 pm

1 stop9h 37m

$294

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Wed 2/4

4:16 pm-12:55 pm

2 stops19h 39m

Oranjestad Reina Beatrix

Mon 2/9

4:35 pm-3:36 pm

2 stops24h 01m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Fri 2/6

4:16 pm-12:30 pm

2 stops19h 14m

Oranjestad Reina Beatrix

Mon 2/9

4:35 pm-3:36 pm

2 stops24h 01m

$320

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Thu 2/5

4:16 pm-12:55 pm

2 stops19h 39m

Oranjestad Reina Beatrix

Mon 2/9

4:35 pm-3:36 pm

2 stops24h 01m

$320

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Tue 3/17

3:25 pm-12:40 pm

2 stops21h 15m

Punta Cana

Tue 3/31

5:15 pm-2:53 pm

2 stops21h 38m

$331

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

Mon 1/5

4:16 pm-1:56 pm

2 stops20h 40m

Punta Cana

Mon 1/12

6:06 pm-3:36 pm

2 stops22h 30m

$332

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Wed 3/4

4:15 pm-12:55 pm

2 stops19h 40m

Oranjestad Reina Beatrix

Wed 3/11

3:25 pm-2:37 pm

2 stops23h 12m

$368

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Mon 3/2

4:15 pm-12:55 pm

2 stops19h 40m

Oranjestad Reina Beatrix

Wed 3/11

3:25 pm-2:37 pm

2 stops23h 12m

$368

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

Thu 3/5

4:15 pm-12:55 pm

2 stops19h 40m

Oranjestad Reina Beatrix

Tue 3/10

3:25 pm-2:37 pm

2 stops23h 12m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 53 results
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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, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $85). Flying from Worcester, Massachusetts to Caribbean Islands in September is currently the most expensive (average of $147). 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 November 3, 2025.

A simple way to save on the total cost of your ticket is to fly from Worcester, Massachusetts to Caribbean Islands in the evening. If you’re flexible enough to do this you can expect to save up to 71% on your trip compared to booking a flight in the afternoon.

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 November 3, 2025.
See what other customers who have flown with JetBlue 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
7.2
Good
2,907 reviews

Food

6.7

Overall

7.2

Entertainment

7.3

Comfort

7.6

Crew

8.0

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,907 reviews
JetBlue
7.2
Good
2,907 reviews

Food

6.7

Overall

7.2

Entertainment

7.3

Comfort

7.6

Crew

8.0

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

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.

  • How long is the flight from Worcester, Massachusetts to Caribbean Islands?

    There are many flights that can get you from Worcester, Massachusetts to Caribbean Islands in 8h 38m. Fly via American Airlines, Delta, or JetBlue to get the fastest option. Worcester, Massachusetts and Caribbean Islands are separated by a distance of 1681 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 - Santo Domingo Las Americas or Worcester - Oranjestad Reina Beatrix.

  • 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, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean Islands (average of $85). Flying from Worcester, Massachusetts to Caribbean Islands in September is currently the most expensive (average of $147). 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.

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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$540FlexibilityNo cancel feeOn-time62%

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