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Cayman Islands

$72+ Cheap flights from Massachusetts 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Massachusetts to Cayman Islands

Cheapest flights from Massachusetts to Cayman Islands
Explore the most affordable flight options available from Massachusetts to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/217:25 pmBOS - GCM
1 stop17h 11mDelta
Fri 12/263:42 pmGCM - BOS
1 stop7h 29mDelta
Deal found 12/16$320
This Delta deal was found by Cheapflights users on 12/16. 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.
Mon 12/225:40 amBOS - GCM
1 stop6h 56mDelta
Wed 12/311:52 pmGCM - BOS
1 stop7h 16mDelta
Deal found 12/16$346
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:01 amBOS - GCM
1 stop7h 44mUnited Airlines
Mon 12/295:10 pmGCM - BOS
1 stop17h 27mUnited Airlines
Deal found 12/16$352
This Delta deal was found by Cheapflights users on 12/17. 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.
Sun 12/217:25 pmBOS - GCM
1 stop17h 11mDelta
Sun 12/283:42 pmGCM - BOS
1 stop7h 29mDelta
Deal found 12/17$355
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/237:00 amBDL - GCM
1 stop7h 35mAmerican Airlines
Sun 12/283:35 pmGCM - BDL
1 stop8h 18mAmerican Airlines
Deal found 12/17$358
This Delta deal was found by Cheapflights users on 12/15. 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.
Mon 12/225:40 amBOS - GCM
1 stop6h 56mDelta
Tue 12/303:42 pmGCM - BOS
1 stop9h 25mDelta
Deal found 12/15$372
This Delta deal was found by Cheapflights users on 12/17. 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.
Mon 12/227:25 pmBOS - GCM
1 stop17h 11mDelta
Sun 12/283:42 pmGCM - BOS
1 stop9h 25mDelta
Deal found 12/17$381
This JetBlue deal was found by Cheapflights users on 12/16. 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.
Tue 12/236:00 amBDL - GCM
1 stop8h 35mJetBlue
Sun 12/283:40 pmGCM - BDL
1 stop8h 19mJetBlue
Deal found 12/16$389
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/237:05 amBDL - GCM
1 stop7h 22mDelta
Sun 12/283:42 pmGCM - BDL
1 stop7h 54mDelta
Deal found 12/16$392
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/207:00 amBDL - GCM
1 stop8h 00mAmerican Airlines
Mon 12/223:11 pmGCM - BDL
1 stop7h 47mAmerican Airlines
Deal found 12/16$403
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/235:40 amBOS - GCM
1 stop6h 56mDelta
Wed 12/311:52 pmGCM - BOS
1 stop7h 16mDelta
Deal found 12/16$415
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:20 amBOS - GCM
1 stop11h 15mUnited Airlines
Wed 12/315:10 pmGCM - BOS
1 stop6h 44mUnited Airlines
Deal found 12/16$419

Find flight deals from Massachusetts to Cayman Islands

Keep the following information in mind while searching for Massachusetts to Cayman Islands flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(Priceline)

One-way from

$72
(Priceline)

Popular in

December

Cheapest in

March

Average price

$644

Good round-trip deal

$343 or less
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 Massachusetts to Cayman Islands
Search Deals
One-way flight from Massachusetts to Cayman Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 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
Price to beat on a round-trip flight from Massachusetts to Cayman Islands.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 18, 2025.
Use the filters below to find and compare flights from Massachusetts to the Cayman Islands that are best for you.

Fly from

Massachusetts

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/24

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 1/31

5:30 pm-11:49 pm

1 stop6h 19m

$260

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 2/24

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Tue 3/3

2:25 pm-9:51 pm

1 stop7h 26m

$260

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/10

5:34 am-1:38 pm

1 stop8h 04m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:57 pm

1 stop9h 23m

$265

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/10

5:34 am-1:38 pm

1 stop8h 04m

George Town Owen Roberts Intl

Thu 1/15

2:49 pm-11:57 pm

1 stop9h 08m

$265

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 1/6

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 1/10

5:45 pm-10:52 am

2 stops17h 07m

$265

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/31

7:22 pm-1:45 pm

2 stops18h 23m

George Town Owen Roberts Intl

Sat 2/7

2:25 pm-11:49 pm

2 stops9h 24m

$265

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/10

7:22 pm-1:45 pm

2 stops18h 23m

George Town Owen Roberts Intl

Thu 1/29

2:25 pm-9:52 pm

1 stop7h 27m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 1/19

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Fri 1/23

2:25 pm-9:52 pm

1 stop7h 27m

$270

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Fri 2/6

6:50 pm-11:35 am

1 stop16h 45m

George Town Owen Roberts Intl

Thu 2/12

12:55 pm-11:56 pm

1 stop11h 01m

$280

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 6/4

5:34 pm-10:55 am

2 stops18h 21m

George Town Owen Roberts Intl

Mon 6/8

3:15 pm-11:37 am

2 stops19h 22m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 48 results
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Best time to book a flight from Massachusetts to Cayman Islands

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

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Cayman Islands (average of $194). Flying from Massachusetts to Cayman Islands in June is currently the most expensive (average of $419). 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 MA to KY?

Find hourly flight availability from Massachusetts to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

It’s typically best to fly out from Massachusetts to Cayman Islands in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying at noon, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    United Airlines, Spirit Airlines, and American Airlines can get you from Massachusetts to Cayman Islands in just under 7h 15m. Your travel time can differ by up to 9h 30m. The distance from Massachusetts to Cayman Islands is about 1704 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Massachusetts to Cayman Islands one-way?

    One-way options have recently been found by users for as low as $54 on Delta. Other airlines that offer cheap prices include JetBlue from $89 and United Airlines from $90 one-way.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Cayman Islands (average of $194). Flying from Massachusetts to Cayman Islands in June is currently the most expensive (average of $419). 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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Alternative routes for Massachusetts to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Cayman Islands

Discover the top 5 airlines that operate flights from Massachusetts to Cayman Islands. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$128Average$455FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$244Average$374FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$287Average$489FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$349Average$546FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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