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Cayman Islands

$223+ Cheap flights from Worcester, MA (ORH) to the Cayman 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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — GCM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Worcester to Cayman Islands

Cheapest flights from Worcester to Cayman Islands
Explore the most affordable flight options available from Worcester to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Tue 12/307:30 amGCM - ORH
2 stops28h 24mAmerican Airlines
Deal found 12/11$431
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Wed 12/313:11 pmGCM - ORH
2 stops46h 06mAmerican Airlines
Deal found 12/11$445
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Sun 12/284:30 pmGCM - ORH
2 stops44h 47mAmerican Airlines
Deal found 12/11$452
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/201:45 pmORH - GCM
2 stops46h 05mAmerican Airlines
Tue 12/303:45 pmGCM - ORH
2 stops20h 09mAmerican Airlines
Deal found 12/11$513
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/201:45 pmORH - GCM
2 stops46h 05mAmerican Airlines
Sun 12/283:35 pmGCM - ORH
2 stops21h 42mAmerican Airlines
Deal found 12/11$518
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/201:45 pmORH - GCM
2 stops46h 05mAmerican Airlines
Wed 12/313:11 pmGCM - ORH
2 stops22h 11mAmerican Airlines
Deal found 12/11$519
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/201:45 pmORH - GCM
2 stops46h 05mAmerican Airlines
Thu 1/14:30 pmGCM - ORH
2 stops20h 47mAmerican Airlines
Deal found 12/11$572
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/241:36 pmORH - GCM
2 stops24h 59mAmerican Airlines
Tue 12/303:45 pmGCM - ORH
2 stops20h 09mAmerican Airlines
Deal found 12/11$617
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/241:36 pmORH - GCM
2 stops24h 59mAmerican Airlines
Sun 12/283:35 pmGCM - ORH
2 stops21h 42mAmerican Airlines
Deal found 12/11$622
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/241:36 pmORH - GCM
2 stops24h 59mAmerican Airlines
Wed 12/313:11 pmGCM - ORH
2 stops22h 11mAmerican Airlines
Deal found 12/11$623
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/231:45 pmORH - GCM
2 stops24h 50mAmerican Airlines
Sat 12/273:45 pmGCM - ORH
2 stops21h 32mAmerican Airlines
Deal found 12/11$637
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/221:45 pmORH - GCM
2 stops22h 12mAmerican Airlines
Mon 12/2912:50 pmGCM - ORH
2 stops24h 27mAmerican Airlines
Deal found 12/11$642

Find flight deals from Worcester to Cayman Islands

Keep the following information in mind while searching for Worcester to Cayman Islands flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$301
(American Airlines)

One-way from

$223
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$644
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
Search Deals
From Worcester to Cayman Islands
Search Deals
One-way flight from Worcester to Cayman Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester to Cayman 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 December 12, 2025.
Use the filters below to find and compare flights from Worcester to the Cayman Islands that are best for you.

Fly from

Worcester

Fly to

Cayman Islands

Route

Depart

Return

Price

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 1/24

2:23 pm-11:26 am

2 stops21h 03m

George Town Owen Roberts Intl

Sat 1/31

3:51 pm-1:53 pm

2 stops22h 02m

$301

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Tue 12/23

1:45 pm-2:35 pm

2 stops24h 50m

George Town Owen Roberts Intl

Mon 12/29

12:50 pm-1:17 pm

2 stops24h 27m

$431

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Tue 12/23

1:45 pm-2:35 pm

2 stops24h 50m

George Town Owen Roberts Intl

Tue 12/30

7:30 am-11:54 am

2 stops28h 24m

$431

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Tue 12/23

1:45 pm-2:35 pm

2 stops24h 50m

George Town Owen Roberts Intl

Wed 12/31

3:11 pm-1:17 pm

2 stops46h 06m

$445

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Tue 12/23

1:45 pm-2:35 pm

2 stops24h 50m

George Town Owen Roberts Intl

Sun 12/28

4:30 pm-1:17 pm

2 stops44h 47m

$452

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Wed 12/24

1:36 pm-2:35 pm

2 stops24h 59m

George Town Owen Roberts Intl

Tue 12/30

3:45 pm-11:54 am

2 stops20h 09m

$617

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Wed 12/24

1:36 pm-2:35 pm

2 stops24h 59m

George Town Owen Roberts Intl

Mon 12/29

12:50 pm-1:17 pm

2 stops24h 27m

$623

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Wed 12/24

1:36 pm-2:35 pm

2 stops24h 59m

George Town Owen Roberts Intl

Wed 12/31

3:11 pm-1:22 pm

2 stops22h 11m

$623

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Tue 12/23

1:45 pm-2:35 pm

2 stops24h 50m

George Town Owen Roberts Intl

Sat 12/27

3:45 pm-1:17 pm

2 stops21h 32m

$637

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 12/22

1:45 pm-11:57 am

2 stops22h 12m

George Town Owen Roberts Intl

Mon 12/29

12:50 pm-1:17 pm

2 stops24h 27m

$642

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 16 results
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Best time to book a flight from Worcester to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman 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 the Cayman Islands

What is the cheapest month to book a flight from Worcester, Massachusetts to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Cayman Islands (average of $194). Flying from Worcester, Massachusetts to Cayman Islands in July is currently the most expensive (average of $389). 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.

Related info for your journey

Find useful and relevant information for your journey from Worcester to Cayman 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 Cayman 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 Cayman Islands.

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

    American Airlines can get you from Worcester, Massachusetts to Cayman Islands in just under 21h 03m. Your travel time can differ by up to . The distance between Worcester, Massachusetts and Cayman Islands is about 1680 mi.

  • Can I find deals for flights from Worcester to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Worcester to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Worcester to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Worcester to Cayman Islands.

  • Can I find deals for business class flights from Worcester to Cayman Islands?

    Yes. Cheapflights offers flight deals from Worcester to Cayman 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 Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Worcester, Massachusetts to Cayman Islands (average of $194). Flying from Worcester, Massachusetts to Cayman Islands in July is currently the most expensive (average of $389). 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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