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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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$420
(Delta)

One-way from

$158
(Delta)

Popular in

February

Cheapest in

January

Average price

$510

Good round-trip deal

$515 or less

Good one-way deal

$348 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 May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 5/1. 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.
Fri 7/45:35 amBOS - GCM
1 stop6h 50mDelta
Tue 7/812:40 pmGCM - BOS
1 stop9h 02mDelta
Deal found 5/1$420
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2812:15 pmBOS - GCM
1 stop24h 40mAir Canada
Thu 6/512:50 pmGCM - BOS
2 stops24h 42mAir Canada
Deal found 4/30$424
This JetBlue deal was found by Cheapflights users on 4/30. 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 4/30$425
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/275:44 amBDL - GCM
1 stop8h 26mAmerican Airlines
Fri 6/62:05 pmGCM - BDL
2 stops17h 57mAmerican Airlines
Deal found 4/30$438
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/285:00 amBOS - GCM
1 stop7h 20mAmerican Airlines
Mon 6/212:25 pmGCM - BOS
1 stop9h 15mAmerican Airlines
Deal found 5/1$440
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/75:15 amBOS - GCM
1 stop8h 15mUnited Airlines
Wed 5/141:35 pmGCM - BOS
2 stops20h 03mUnited Airlines
Deal found 4/30$454
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 7/186:00 amBDL - GCM
1 stop6h 25mDelta
Fri 7/2512:40 pmGCM - BDL
1 stop8h 41mDelta
Deal found 4/30$459
This Southwest deal was found by Cheapflights users on 5/1. 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.
Thu 5/85:20 amALB - GCM
1 stop7h 30mSouthwest
Thu 5/1512:45 pmGCM - ALB
1 stop8h 20mSouthwest
Deal found 5/1$484
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 5/85:36 pmALB - GCM
2 stops18h 44mAmerican Airlines
Thu 5/1512:25 pmGCM - ALB
1 stop11h 33mAmerican Airlines
Deal found 5/1$488
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 7/45:20 amBOS - GCM
2 stops7h 30mSouthwest
Tue 7/812:45 pmGCM - BOS
2 stops10h 10mSouthwest
Deal found 4/30$489
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/299:46 amBOS - GCM
1 stop26h 54mMultiple Airlines
Sun 6/112:40 pmGCM - BOS
1 stop19h 09mMultiple Airlines
Deal found 4/30$535
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 5/89:35 amALB - GCM
2 stops27h 55mUnited Airlines
Thu 5/151:35 pmGCM - ALB
2 stops23h 41mUnited Airlines
Deal found 5/1$578

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 May 1, 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

Fri 7/4

5:35 am-11:25 am

1 stop6h 50m

George Town Owen Roberts Intl

Tue 7/8

12:40 pm-10:42 pm

1 stop9h 02m

$420

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 5/28

12:15 pm-11:55 am

1 stop24h 40m

George Town Owen Roberts Intl

Thu 6/5

12:50 pm-2:32 pm

2 stops24h 42m

$424

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 5/27

5:44 am-1:10 pm

1 stop8h 26m

George Town Owen Roberts Intl

Fri 6/6

2:05 pm-9:02 am

2 stops17h 57m

$438

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 5/28

5:00 am-11:20 am

1 stop7h 20m

George Town Owen Roberts Intl

Mon 6/2

12:25 pm-10:40 pm

1 stop9h 15m

$440

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Fri 7/18

6:00 am-11:25 am

1 stop6h 25m

George Town Owen Roberts Intl

Fri 7/25

12:40 pm-10:21 pm

1 stop8h 41m

$459

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 7/4

5:20 am-11:50 am

2 stops7h 30m

George Town Owen Roberts Intl

Tue 7/8

12:45 pm-11:55 pm

2 stops10h 10m

$489

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 6/28

6:55 pm-11:15 am

2 stops17h 20m

George Town Owen Roberts Intl

Wed 7/2

12:25 pm-10:36 pm

1 stop9h 11m

$490

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 6/14

6:55 am-12:35 pm

1 stop6h 40m

George Town Owen Roberts Intl

Fri 6/20

1:35 pm-11:12 am

2 stops20h 37m

$494

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 5/29

9:46 am-11:40 am

1 stop26h 54m

George Town Owen Roberts Intl

Sun 6/1

12:40 pm-8:49 am

1 stop19h 09m

$535

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Sat 6/14

6:10 am-1:30 pm

1 stop8h 20m

George Town Owen Roberts Intl

Sat 6/21

4:45 pm-2:17 pm

2 stops20h 32m

$632

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 24 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 May 1, 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 May 1, 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
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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
2,923 reviews
Southwest
8.0
Very good
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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
4,293 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Overall

8.0

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 $168 and American Airlines from $178 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
DeltaCheapest$252Average$446FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$473FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$454FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$320Average$524FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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