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Cayman Islands

$83+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap 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 septiembre 17, 2025.

Round-trip from

$270
(United Airlines)

One-way from

$83
(Southwest)

Popular in

February

Cheapest in

January

Average price

$512

Good round-trip deal

$425 or less
From Massachusetts to Cayman Islands
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One-way flight from Massachusetts to Cayman Islands
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High demand for flights, 8% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Massachusetts to Cayman Islands.
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Find 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 septiembre 17, 2025.

This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/296:00 amBOS - GCM
1 stop7h 15mUnited Airlines
lun. 12/85:45 pmGCM - BOS
1 stop18h 36mUnited Airlines
Deal found 9/17$270
This United Airlines deal was found by Cheapflights users on 9/14. 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.
sáb. 12/66:00 amBOS - GCM
1 stop7h 45mUnited Airlines
sáb. 12/202:25 pmGCM - BOS
1 stop8h 23mUnited Airlines
Deal found 9/14$282
This United Airlines deal was found by Cheapflights users on 9/16. 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.
sáb. 11/87:00 amBOS - GCM
1 stop9h 20mUnited Airlines
sáb. 11/152:25 pmGCM - BOS
1 stop8h 23mUnited Airlines
Deal found 9/16$294
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/65:45 amBOS - GCM
2 stops8h 37mAmerican Airlines
lun. 1/122:00 pmGCM - BOS
1 stop8h 26mAmerican Airlines
Deal found 9/15$302
This United Airlines deal was found by Cheapflights users on 9/16. 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.
dom. 11/306:02 amBOS - GCM
1 stop7h 13mUnited Airlines
sáb. 12/65:45 pmGCM - BOS
2 stops17h 04mUnited Airlines
Deal found 9/16$311
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/137:00 amBOS - GCM
1 stop9h 30mUnited Airlines
vie. 11/145:45 pmGCM - BOS
2 stops16h 49mUnited Airlines
Deal found 9/15$314
This JetBlue deal was found by Cheapflights users on 9/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/17:22 amBOS - GCM
Nonstop4h 28mJetBlue
sáb. 11/812:54 pmGCM - BOS
Nonstop4h 11mJetBlue
Deal found 9/17$315
This Delta deal was found by Cheapflights users on 9/16. 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.
dom. 11/95:40 amBOS - GCM
1 stop6h 55mDelta
mar. 11/181:50 pmGCM - BOS
1 stop11h 32mDelta
Deal found 9/16$323
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/215:30 amBOS - GCM
1 stop6h 40mAmerican Airlines
sáb. 10/258:25 amGCM - BOS
1 stop11h 28mAmerican Airlines
Deal found 9/15$330
This American Airlines deal was found by Cheapflights users on 9/16. 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.
sáb. 11/86:45 amBOS - GCM
1 stop8h 15mAmerican Airlines
mar. 11/119:00 amGCM - BOS
1 stop15h 51mAmerican Airlines
Deal found 9/16$331
This American Airlines deal was found by Cheapflights users on 9/17. 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.
vie. 12/55:00 amBDL - GCM
2 stops15h 15mAmerican Airlines
mié. 12/103:45 pmGCM - BDL
1 stop8h 13mAmerican Airlines
Deal found 9/17$332
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/46:00 amBDL - GCM
1 stop8h 55mJetBlue
mar. 12/93:55 pmGCM - BDL
1 stop8h 04mJetBlue
Deal found 9/15$378

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 septiembre 17, 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

sáb. 11/29

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

mar. 12/9

5:45 pm-12:21 pm

1 stop18h 36m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mar. 11/18

5:40 am-12:35 pm

1 stop6h 55m

George Town Owen Roberts Intl

mar. 11/25

1:50 pm-1:22 am

1 stop11h 32m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 11/29

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

sáb. 12/6

2:25 pm-9:58 pm

1 stop7h 33m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mar. 11/11

8:55 pm-12:35 pm

1 stop15h 40m

George Town Owen Roberts Intl

mar. 11/18

1:50 pm-11:21 pm

1 stop9h 31m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

vie. 11/28

5:40 am-12:35 pm

1 stop6h 55m

George Town Owen Roberts Intl

mié. 12/10

1:50 pm-1:21 am

1 stop11h 31m

$270

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 12/6

6:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

sáb. 12/20

2:25 pm-10:48 pm

1 stop8h 23m

$282

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 11/8

7:00 am-4:20 pm

1 stop9h 20m

George Town Owen Roberts Intl

sáb. 11/15

2:25 pm-10:48 pm

1 stop8h 23m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 11/1

7:22 am-10:50 am

Nonstop4h 28m

George Town Owen Roberts Intl

sáb. 11/8

12:54 pm-5:05 pm

Nonstop4h 11m

$315

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

vie. 2/6

5:43 am-2:00 pm

1 stop8h 17m

George Town Owen Roberts Intl

jue. 2/12

1:35 pm-12:20 am

1 stop10h 45m

$328

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 11/15

6:45 am-3:00 pm

1 stop8h 15m

George Town Owen Roberts Intl

jue. 11/20

12:59 pm-9:40 pm

1 stop8h 41m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 44 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 $467). Flying from Massachusetts to Cayman Islands in March is currently the most expensive (average of $594). 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 septiembre 17, 2025.

When flying from Massachusetts to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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, Delta, and American Airlines can get you from Massachusetts to Cayman Islands in just under 6h 55m. Your travel time can differ by up to 1h 22m. 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 $83 on Southwest. Other airlines that offer cheap prices include Delta from $90 and United Airlines from $95 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 $467). Flying from Massachusetts to Cayman Islands in March is currently the most expensive (average of $594). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 6 airlines flying from Massachusetts to Cayman Islands

Discover the top 6 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$463FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$257Average$454FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$427FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$314Average$534FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$457Average$559FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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