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Caribbean Islands

$124+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
mar. 6 — mar. 131
fre. 3/6
fre. 3/13
1 adult, Economy
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Cheap 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 februar 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/2. 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.
lør. 2/281:30 pm
ORH
-
SJU
1 stop10h 22m
American Airlines
ons. 3/410:50 am
SJU
-
ORH
2 stops27h 15m
American Airlines
Deal found 2/2$232
This American Airlines deal was found by Cheapflights users on 2/3. 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.
tir. 3/101:44 pm
ORH
-
SJU
2 stops15h 44m
American Airlines
tor. 3/125:00 am
SJU
-
ORH
1 stop8h 19m
American Airlines
Deal found 2/3$233
This American Airlines deal was found by Cheapflights users on 2/4. 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.
lør. 3/71:30 pm
ORH
-
STT
2 stops20h 36m
American Airlines
man. 3/912:02 pm
STT
-
ORH
2 stops25h 17m
American Airlines
Deal found 2/4$274
This KAYAK deal was found by Cheapflights users on 2/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 3/304:55 pm
ORH
-
SJU
1 stop7h 10m
JetBlue
ons. 4/89:25 am
SJU
-
ORH
1 stop6h 31m
JetBlue
Deal found 2/2$290
This American Airlines deal was found by Cheapflights users on 2/2. 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.
tir. 3/311:44 pm
ORH
-
SJU
2 stops21h 12m
American Airlines
ons. 4/87:00 pm
SJU
-
ORH
2 stops19h 14m
American Airlines
Deal found 2/2$292
This American Airlines deal was found by Cheapflights users on 2/2. 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.
lør. 10/317:43 pm
ORH
-
PUJ
1 stop16h 11m
American Airlines
fre. 11/65:33 pm
PUJ
-
ORH
2 stops22h 31m
American Airlines
Deal found 2/2$319
This American Airlines deal was found by Cheapflights users on 2/4. 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.
fre. 9/257:33 pm
ORH
-
PUJ
2 stops19h 02m
American Airlines
ons. 9/305:20 pm
PUJ
-
ORH
2 stops27h 47m
American Airlines
Deal found 2/4$323
This American Airlines deal was found by Cheapflights users on 2/2. 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.
man. 4/132:39 pm
ORH
-
NAS
2 stops20h 20m
American Airlines
fre. 4/176:03 pm
NAS
-
ORH
2 stops20h 11m
American Airlines
Deal found 2/2$330
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
søn. 2/224:30 pm
ORH
-
AUA
2 stops19h 25m
Delta
man. 3/24:35 pm
AUA
-
ORH
2 stops23h 58m
Delta
Deal found 2/3$330
This American Airlines deal was found by Cheapflights users on 2/2. 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.
man. 2/92:18 pm
ORH
-
AUA
1 stop22h 41m
American Airlines
man. 2/165:55 pm
AUA
-
ORH
2 stops20h 10m
American Airlines
Deal found 2/2$331
This KAYAK deal was found by Cheapflights users on 2/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tir. 3/34:59 pm
ORH
-
SJU
1 stop7h 00m
JetBlue
tor. 3/58:00 am
SJU
-
ORH
1 stop9h 02m
JetBlue
Deal found 2/2$332
This American Airlines deal was found by Cheapflights users on 2/3. 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.
tir. 3/171:44 pm
ORH
-
PUJ
2 stops25h 10m
American Airlines
tir. 3/314:43 pm
PUJ
-
ORH
2 stops20h 36m
American Airlines
Deal found 2/3$336

Find 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 februar 4, 2026.

Round-trip from

$232
(American Airlines)

One-way from

$124
(Delta)

Popular in

December

Cheapest in

January

Average price

$288
From Worcester to Caribbean Islands
Search Deals
One-way flight from Worcester to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 februar 4, 2026.
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

lør. 2/28

1:30 pm-12:52 am

1 stop10h 22m

San Juan Luis Munoz Marin Intl

ons. 3/4

10:50 am-1:05 pm

2 stops27h 15m

$232

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

tir. 3/10

1:44 pm-5:28 am

2 stops15h 44m

San Juan Luis Munoz Marin Intl

tor. 3/12

5:00 am-1:19 pm

1 stop8h 19m

$233

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

tir. 3/17

1:44 pm-2:54 pm

2 stops25h 10m

Saint Thomas Island Cyril E King

tir. 3/24

5:25 pm-1:19 pm

2 stops19h 54m

$274

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

lør. 3/7

1:30 pm-11:06 am

2 stops20h 36m

Saint Thomas Island Cyril E King

tir. 3/10

5:25 pm-1:19 pm

2 stops19h 54m

$274

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

lør. 3/7

1:30 pm-11:06 am

2 stops20h 36m

Saint Thomas Island Cyril E King

man. 3/9

12:02 pm-1:19 pm

2 stops25h 17m

$274

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

tir. 3/17

1:44 pm-2:54 pm

2 stops25h 10m

Saint Thomas Island Cyril E King

man. 3/23

5:25 pm-1:19 pm

2 stops19h 54m

$274

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

lør. 3/7

1:30 pm-11:06 am

2 stops20h 36m

Saint Thomas Island Cyril E King

søn. 3/8

3:40 pm-1:19 pm

2 stops21h 39m

$274

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

man. 3/30

4:55 pm-12:05 am

1 stop7h 10m

San Juan Luis Munoz Marin Intl

ons. 4/8

9:25 am-3:56 pm

1 stop6h 31m

$290

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

man. 3/30

1:44 pm-11:52 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

ons. 4/8

7:00 pm-2:14 pm

2 stops19h 14m

$292

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

tir. 3/31

1:44 pm-11:52 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

tor. 4/9

11:59 pm-2:14 pm

2 stops14h 15m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 59 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 $88). Flying from Worcester, Massachusetts to Caribbean Islands in July is currently the most expensive (average of $142). 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.

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 februar 4, 2026.
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
2,893 reviews

Crew

8.0

Boarding

7.4

Food

6.6

Comfort

7.5

Entertainment

7.2

Overall

7.2

Reviews

1 / 20
4.0
Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.
JetBlue
7.2
Good
2,893 reviews
JetBlue
7.2
Good
2,893 reviews

Crew

8.0

Boarding

7.4

Food

6.6

Comfort

7.5

Entertainment

7.2

Overall

7.2

Reviews

1 / 20
4.0
Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.

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 7h 10m. Fly via American Airlines, JetBlue, or Delta 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 - Punta Cana or Worcester - Nassau Intl.

  • 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 $88). Flying from Worcester, Massachusetts to Caribbean Islands in July is currently the most expensive (average of $142). 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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