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Cayman Islands

$363+ Cheap flights from Worcester, MA (ORH) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — GCM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

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.
Mon 4/132:39 pm
ORH
-
GCM
2 stops21h 21m
American Airlines
Sat 4/1812:40 pm
GCM
-
ORH
1 stop24h 34m
American Airlines
Deal found 1/27$363
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.
Sun 4/122:39 pm
ORH
-
GCM
2 stops45h 56m
American Airlines
Sat 4/1812:40 pm
GCM
-
ORH
1 stop24h 34m
American Airlines
Deal found 1/27$377
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.
Sun 4/122:39 pm
ORH
-
GCM
2 stops21h 53m
American Airlines
Thu 4/1612:35 pm
GCM
-
ORH
2 stops24h 39m
American Airlines
Deal found 1/27$454
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.
Sat 4/112:39 pm
ORH
-
GCM
2 stops23h 32m
American Airlines
Sat 4/1812:40 pm
GCM
-
ORH
1 stop24h 34m
American Airlines
Deal found 1/27$512
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.
Fri 3/131:44 pm
ORH
-
GCM
1 stop22h 11m
American Airlines
Fri 3/207:45 am
GCM
-
ORH
2 stops28h 34m
American Airlines
Deal found 1/28$519
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.
Sat 4/112:39 pm
ORH
-
GCM
2 stops21h 53m
American Airlines
Thu 4/1612:35 pm
GCM
-
ORH
2 stops24h 39m
American Airlines
Deal found 1/27$524
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.
Sat 4/112:39 pm
ORH
-
GCM
2 stops23h 32m
American Airlines
Wed 4/152:10 pm
GCM
-
ORH
2 stops23h 04m
American Airlines
Deal found 1/27$526
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.
Sun 4/122:39 pm
ORH
-
GCM
2 stops45h 56m
American Airlines
Wed 4/1512:00 pm
GCM
-
ORH
2 stops25h 14m
American Airlines
Deal found 1/27$534
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.
Mon 4/132:39 pm
ORH
-
GCM
2 stops21h 21m
American Airlines
Fri 4/1712:35 pm
GCM
-
ORH
2 stops24h 39m
American Airlines
Deal found 1/27$535
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.
Sun 4/122:39 pm
ORH
-
GCM
2 stops45h 56m
American Airlines
Fri 4/1712:35 pm
GCM
-
ORH
2 stops24h 39m
American Airlines
Deal found 1/27$539

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$363
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$408
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
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 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 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 January 29, 2026.
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

Mon 4/13

2:39 pm-11:00 am

2 stops21h 21m

George Town Owen Roberts Intl

Sat 4/18

12:40 pm-2:14 pm

1 stop24h 34m

$363

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 4/13

2:39 pm-11:00 am

2 stops21h 21m

George Town Owen Roberts Intl

Thu 4/16

12:35 pm-2:14 pm

2 stops24h 39m

$375

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Mon 4/13

2:39 pm-11:00 am

2 stops21h 21m

George Town Owen Roberts Intl

Wed 4/15

2:10 pm-2:14 pm

2 stops23h 04m

$377

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sun 4/12

2:39 pm-11:35 am

2 stops45h 56m

George Town Owen Roberts Intl

Sat 4/18

4:03 pm-2:14 pm

2 stops21h 11m

$381

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sun 4/12

2:39 pm-11:32 am

2 stops21h 53m

George Town Owen Roberts Intl

Thu 4/16

12:35 pm-2:14 pm

2 stops24h 39m

$454

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 4/11

2:39 pm-1:11 pm

2 stops23h 32m

George Town Owen Roberts Intl

Sat 4/18

12:40 pm-2:14 pm

1 stop24h 34m

$512

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Fri 3/13

1:44 pm-10:55 am

1 stop22h 11m

George Town Owen Roberts Intl

Fri 3/20

7:45 am-1:19 pm

2 stops28h 34m

$519

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 4/11

2:39 pm-11:32 am

2 stops21h 53m

George Town Owen Roberts Intl

Thu 4/16

12:35 pm-2:14 pm

2 stops24h 39m

$524

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sat 4/11

2:39 pm-1:11 pm

2 stops23h 32m

George Town Owen Roberts Intl

Wed 4/15

2:10 pm-2:14 pm

2 stops23h 04m

$526

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

Sun 4/12

2:39 pm-11:35 am

2 stops45h 56m

George Town Owen Roberts Intl

Wed 4/15

12:00 pm-2:14 pm

2 stops25h 14m

$534

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 $72). 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 21m. 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 $72). 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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