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$107+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheap 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 enero 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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.
vie. 4/102:39 pm
ORH
-
SJU
1 stop7h 26m
American Airlines
vie. 4/176:00 am
SJU
-
ORH
1 stop8h 14m
American Airlines
Deal found 1/28$288
This American Airlines deal was found by Cheapflights users on 1/28. 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.
dom. 4/122:39 pm
ORH
-
SJU
2 stops18h 34m
American Airlines
vie. 4/176:00 am
SJU
-
ORH
1 stop8h 14m
American Airlines
Deal found 1/28$292
This American Airlines deal was found by Cheapflights users on 1/28. 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.
vie. 5/82:39 pm
ORH
-
SJU
1 stop7h 26m
American Airlines
mar. 5/126:00 am
SJU
-
ORH
1 stop8h 14m
American Airlines
Deal found 1/28$297
This JetBlue deal was found by Cheapflights users on 1/27. 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.
mié. 2/254:59 pm
ORH
-
SJU
1 stop7h 00m
JetBlue
mié. 3/48:00 am
SJU
-
ORH
1 stop9h 02m
JetBlue
Deal found 1/27$298
This American Airlines deal was found by Cheapflights users on 1/27. 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.
dom. 3/151:44 pm
ORH
-
SJU
2 stops19h 16m
American Airlines
mié. 3/181:44 pm
SJU
-
ORH
2 stops23h 35m
American Airlines
Deal found 1/27$301
This American Airlines deal was found by Cheapflights users on 1/27. 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.
mar. 3/241:44 pm
ORH
-
AUA
2 stops21h 49m
American Airlines
mar. 3/314:50 pm
AUA
-
ORH
2 stops20h 29m
American Airlines
Deal found 1/27$314
This American Airlines deal was found by Cheapflights users on 1/27. 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.
mar. 2/32:18 pm
ORH
-
SDQ
2 stops21h 03m
American Airlines
mar. 2/245:07 pm
SDQ
-
ORH
2 stops20h 58m
American Airlines
Deal found 1/27$320
This Delta deal was found by Cheapflights users on 1/28. 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.
mié. 2/114:16 pm
ORH
-
AUA
2 stops19h 39m
Delta
lun. 2/164:35 pm
AUA
-
ORH
2 stops23h 58m
Delta
Deal found 1/28$322
This American Airlines deal was found by Cheapflights users on 1/28. 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.
mié. 2/251:30 pm
ORH
-
NAS
2 stops20h 03m
American Airlines
mié. 3/410:13 am
NAS
-
ORH
2 stops26h 52m
American Airlines
Deal found 1/28$326
This Delta deal was found by Cheapflights users on 1/27. 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.
mié. 1/284:16 pm
ORH
-
AUA
2 stops19h 39m
Delta
mar. 2/34:35 pm
AUA
-
ORH
2 stops24h 01m
Delta
Deal found 1/27$330
This American Airlines deal was found by Cheapflights users on 1/27. 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.
jue. 2/261:30 pm
ORH
-
NAS
2 stops22h 18m
American Airlines
dom. 3/13:44 pm
NAS
-
ORH
2 stops21h 21m
American Airlines
Deal found 1/27$331
This American Airlines deal was found by Cheapflights users on 1/28. 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.
mar. 6/305:17 pm
ORH
-
SJU
2 stops16h 16m
American Airlines
mar. 7/77:09 pm
SJU
-
ORH
2 stops21h 43m
American Airlines
Deal found 1/28$332

Find flight deals from Worcester to Caribbean

Keep the following information in mind while searching for Worcester to Caribbean flight deals. Data was last updated enero 29, 2026.

Round-trip from

$288
(American Airlines)

One-way from

$107
(Delta)

Popular in

December

Cheapest in

January

Average price

$254
From Worcester to Caribbean
Search Deals
One-way flight from Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($28 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 January 2026
Search Deals

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 enero 29, 2026.
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

dom. 4/12

2:39 pm-10:05 pm

1 stop7h 26m

San Juan Luis Munoz Marin Intl

vie. 4/17

6:00 am-2:14 pm

1 stop8h 14m

$288

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

sáb. 4/11

2:39 pm-10:05 pm

1 stop7h 26m

San Juan Luis Munoz Marin Intl

vie. 4/17

6:00 am-2:14 pm

1 stop8h 14m

$288

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

vie. 4/10

2:39 pm-10:05 pm

1 stop7h 26m

San Juan Luis Munoz Marin Intl

vie. 4/17

6:00 am-2:14 pm

1 stop8h 14m

$288

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

mié. 2/25

4:59 pm-12:59 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:00 am-4:02 pm

1 stop9h 02m

$298

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

mar. 3/24

1:44 pm-11:33 am

2 stops21h 49m

Oranjestad Reina Beatrix

mar. 3/31

4:50 pm-1:19 pm

2 stops20h 29m

$314

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

mié. 2/11

4:16 pm-12:55 pm

2 stops19h 39m

Oranjestad Reina Beatrix

lun. 2/16

4:35 pm-3:33 pm

2 stops23h 58m

$322

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

mié. 2/25

1:30 pm-9:33 am

2 stops20h 03m

Nassau Intl

mié. 3/4

10:13 am-1:05 pm

2 stops26h 52m

$326

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

jue. 2/26

1:30 pm-11:48 am

2 stops22h 18m

Nassau Intl

dom. 3/1

3:44 pm-1:05 pm

2 stops21h 21m

$331

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

mar. 6/30

5:17 pm-9:33 am

2 stops16h 16m

San Juan Luis Munoz Marin Intl

mar. 7/7

7:09 pm-4:52 pm

2 stops21h 43m

$332

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

mar. 3/17

1:44 pm-1:30 pm

2 stops23h 46m

Punta Cana

mar. 3/31

4:43 pm-1:19 pm

2 stops20h 36m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $88). Flying from Worcester, Massachusetts to Caribbean 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.

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 enero 29, 2026.
Read reviews from past customers who have flown JetBlue from Worcester to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,891 reviews

Boarding

7.4

Food

6.6

Overall

7.2

Crew

8.0

Entertainment

7.2

Comfort

7.5

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
2,891 reviews
JetBlue
7.2
Good
2,891 reviews

Boarding

7.4

Food

6.6

Overall

7.2

Crew

8.0

Entertainment

7.2

Comfort

7.5

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. 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.

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

    Departing from Worcester, Massachusetts to Caribbean will take you 7h. The distance from Worcester, Massachusetts to Caribbean is about 1681 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Worcester, Massachusetts to Caribbean?

    While some choose either Worcester - Oranjestad Reina Beatrix 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, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Caribbean (average of $88). Flying from Worcester, Massachusetts to Caribbean 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.

See more FAQs

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