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Cayman Islands

$158+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$352
(Southwest)

One-way from

$158
(Delta)

Popular in

February

Cheapest in

January

Average price

$598

Good round-trip deal

$515 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
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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, 2% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Massachusetts to Cayman Islands.
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Price to beat on a one-way 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 April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:30 amBOS - GCM
1 stop7h 45mSouthwest
Sat 5/241:10 pmGCM - BOS
1 stop9h 15mSouthwest
Deal found 4/23$352
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 5/246:00 amBOS - GCM
2 stops10h 05mUnited Airlines
Sat 5/314:09 pmGCM - BOS
2 stops16h 47mUnited Airlines
Deal found 4/22$356
This JetBlue deal was found by Cheapflights users on 4/22. 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.
Sat 11/110:13 amBOS - GCM
Nonstop4h 22mJetBlue
Sat 11/83:55 pmGCM - BOS
Nonstop4h 10mJetBlue
Deal found 4/22$425
This American Airlines deal was found by Cheapflights users on 4/23. 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 11/86:40 amBOS - GCM
1 stop9h 15mAmerican Airlines
Tue 11/112:20 pmGCM - BOS
1 stop6h 28mAmerican Airlines
Deal found 4/23$438
This Delta deal was found by Cheapflights users on 4/23. 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 8/256:00 amALB - GCM
1 stop6h 31mDelta
Thu 9/1112:53 pmGCM - ALB
1 stop9h 41mDelta
Deal found 4/23$450
This Delta deal was found by Cheapflights users on 4/22. 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 4/295:40 amBOS - GCM
1 stop6h 42mDelta
Sat 5/101:03 pmGCM - BOS
1 stop8h 47mDelta
Deal found 4/22$450
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/277:20 pmBDL - GCM
1 stop17h 00mAmerican Airlines
Fri 6/62:05 pmGCM - BDL
2 stops17h 30mAmerican Airlines
Deal found 4/23$515
This American Airlines deal was found by Cheapflights users on 4/23. 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 8/266:16 amALB - GCM
1 stop5h 44mAmerican Airlines
Thu 9/1112:45 pmGCM - ALB
1 stop8h 30mAmerican Airlines
Deal found 4/23$518
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 10/114:55 pmBDL - GCM
2 stops20h 35mUnited Airlines
Sat 10/181:35 pmGCM - BDL
2 stops20h 13mUnited Airlines
Deal found 4/23$542
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/244:15 pmBOS - GCM
1 stop20h 25mMultiple Airlines
Sun 7/274:45 pmGCM - BOS
1 stop16h 45mMultiple Airlines
Deal found 4/22$563
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/31:38 pmORH - GCM
2 stops22h 31mAmerican Airlines
Sat 5/103:05 pmGCM - ORH
2 stops21h 11mAmerican Airlines
Deal found 4/23$580
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 12/66:00 amBDL - GCM
1 stop6h 37mDelta
Mon 12/82:02 pmGCM - BDL
1 stop9h 44mDelta
Deal found 4/22$582

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 April 24, 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 5/17

5:30 am-12:15 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sat 5/24

1:10 pm-11:25 pm

1 stop9h 15m

$352

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/24

6:00 am-3:05 pm

2 stops10h 05m

George Town Owen Roberts Intl

Sat 5/31

4:09 pm-9:56 am

2 stops16h 47m

$356

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/10

7:49 am-2:15 pm

1 stop7h 26m

George Town Owen Roberts Intl

Sat 5/17

12:25 pm-10:51 pm

1 stop9h 26m

$440

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Mon 8/25

6:00 am-11:31 am

1 stop6h 31m

George Town Owen Roberts Intl

Thu 9/11

12:53 pm-11:34 pm

1 stop9h 41m

$450

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 4/29

5:40 am-11:22 am

1 stop6h 42m

George Town Owen Roberts Intl

Tue 5/6

12:47 pm-9:23 pm

1 stop7h 36m

$450

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 5/27

7:20 pm-11:20 am

1 stop17h 00m

George Town Owen Roberts Intl

Fri 6/6

2:05 pm-8:35 am

2 stops17h 30m

$515

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Tue 8/26

6:16 am-11:00 am

1 stop5h 44m

George Town Owen Roberts Intl

Thu 9/11

12:45 pm-10:15 pm

1 stop8h 30m

$518

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Sat 10/11

4:55 pm-12:30 pm

2 stops20h 35m

George Town Owen Roberts Intl

Sat 10/18

1:35 pm-10:48 am

2 stops20h 13m

$542

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 5/6

3:50 pm-4:10 pm

2 stops25h 20m

George Town Owen Roberts Intl

Tue 9/2

11:30 am-12:39 am

3 stops36h 09m

$568

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Fri 6/20

6:00 am-4:00 pm

1 stop11h 00m

George Town Owen Roberts Intl

Sun 6/29

12:40 pm-1:07 pm

2 stops23h 27m

$693

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 27 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 April 24, 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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated April 24, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Massachusetts to Cayman Islands. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $158 on Delta. Other airlines that offer cheap prices include Air Canada from $163 and United Airlines from $174 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

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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 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
DeltaCheapest$252Average$451FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$471FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$453FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$519FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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