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$258+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SJU
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$271
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$303
From Worcester to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 julio 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/28. 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.
lun. 11/243:29 pmORH - SJU
1 stop7h 18mAmerican Airlines
jue. 11/276:30 amSJU - ORH
1 stop9h 23mAmerican Airlines
Deal found 7/28$271
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/173:59 pmORH - PUJ
1 stop17h 41mJetBlue
sáb. 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.
sáb. 9/134:24 pmORH - MBJ
2 stops19h 06mAmerican Airlines
sáb. 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.
mié. 8/273:20 pmORH - PUJ
2 stops22h 55mAmerican Airlines
mié. 9/34:25 pmPUJ - ORH
2 stops23h 34mAmerican Airlines
Deal found 7/30$471
This Delta deal was found by Cheapflights users on 7/28. 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.
jue. 11/133:18 pmORH - PUJ
2 stops20h 20mDelta
mar. 11/184:55 pmPUJ - ORH
2 stops22h 43mDelta
Deal found 7/28$499
This JetBlue deal was found by Cheapflights users on 7/27. 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.
vie. 12/511:57 amORH - SJU
1 stop8h 23mJetBlue
sáb. 12/135:05 amSJU - ORH
1 stop10h 40mJetBlue
Deal found 7/27$505
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.
sáb. 9/132:30 pmORH - MBJ
1 stop22h 35mJetBlue
sáb. 9/2011:30 amMBJ - ORH
1 stop27h 20mJetBlue
Deal found 7/30$542
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.
mar. 10/74:17 pmORH - STT
2 stops19h 43mAmerican Airlines
jue. 10/165:20 pmSTT - ORH
2 stops22h 30mAmerican Airlines
Deal found 7/30$569
This American Airlines deal was found by Cheapflights users on 7/28. 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.
jue. 8/143:20 pmORH - AUA
2 stops44h 00mAmerican Airlines
dom. 8/175:05 pmAUA - ORH
2 stops21h 50mAmerican Airlines
Deal found 7/28$625
This American Airlines deal was found by Cheapflights users on 7/29. 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. 7/303:29 pmORH - NAS
2 stops18h 36mAmerican Airlines
lun. 8/46:35 pmNAS - ORH
2 stops20h 29mAmerican Airlines
Deal found 7/29$697
This JetBlue deal was found by Cheapflights users on 7/29. 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. 8/610:45 amORH - NAS
1 stop6h 23mJetBlue
jue. 8/79:45 amNAS - ORH
1 stop5h 18mJetBlue
Deal found 7/29$855

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 julio 30, 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

mar. 8/12

3:20 pm-10:49 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

sáb. 8/16

7:05 pm-2:55 pm

2 stops19h 50m

$431

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

dom. 8/17

3:59 pm-9:40 am

1 stop17h 41m

Punta Cana

sáb. 8/23

10:35 am-3:03 pm

1 stop28h 28m

$442

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

sáb. 9/13

4:24 pm-10:30 am

2 stops19h 06m

Montego Bay Sangster Intl

sáb. 9/20

2:38 pm-3:58 pm

2 stops24h 20m

$460

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

mié. 8/27

3:20 pm-2:15 pm

2 stops22h 55m

Punta Cana

mié. 9/3

4:25 pm-3:59 pm

2 stops23h 34m

$471

WorcesterPunta Cana

ORH - PUJ

ORHPUJ

Worcester

jue. 11/13

3:18 pm-12:38 pm

2 stops20h 20m

Punta Cana

mar. 11/18

4:55 pm-2:38 pm

2 stops22h 43m

$499

WorcesterMontego Bay

ORH - MBJ

ORHMBJ

Worcester

sáb. 9/13

2:30 pm-12:05 pm

1 stop22h 35m

Montego Bay Sangster Intl

sáb. 9/20

11:30 am-3:50 pm

1 stop27h 20m

$542

WorcesterSaint Thomas Island

ORH - STT

ORHSTT

Worcester

mar. 10/7

4:17 pm-12:00 pm

2 stops19h 43m

Saint Thomas Island Cyril E King

jue. 10/16

5:20 pm-3:50 pm

2 stops22h 30m

$569

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

jue. 8/28

3:59 pm-11:07 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

jue. 9/4

6:04 am-3:50 pm

1 stop9h 46m

$587

WorcesterOranjestad

ORH - AUA

ORHAUA

Worcester

jue. 8/14

3:20 pm-11:20 am

2 stops44h 00m

Oranjestad Reina Beatrix

dom. 8/17

5:05 pm-2:55 pm

2 stops21h 50m

$625

WorcesterNassau

ORH - NAS

ORHNAS

Worcester

lun. 12/29

3:25 pm-1:30 pm

2 stops22h 05m

Nassau Intl

vie. 1/2

2:40 pm-2:53 pm

2 stops24h 13m

$778

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 14 results
1
2

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 julio 30, 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.

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 julio 30, 2025.
Read reviews from past customers who have flown Delta, JetBlue, and American Airlines 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.
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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
7,980 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Overall

8.0

Crew

8.5

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 - Punta Cana or Worcester - Saint Thomas Island Cyril E King, 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$136Average$689FlexibilityNo cancel feeOn-time62%

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