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Cayman Islands

$131+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$400
(Delta)

One-way from

$148
(American Airlines)

Popular in

February

Cheapest in

January

Average price

$533

Good round-trip deal

$495 or less

Good one-way deal

$173 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, 4% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:35 amBOS - GCM
1 stop7h 02mDelta
Fri 8/2912:50 pmGCM - BOS
1 stop11h 30mDelta
Deal found 6/14$400
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 11/87:19 pmBOS - GCM
1 stop16h 41mAmerican Airlines
Tue 11/118:30 amGCM - BOS
1 stop8h 25mAmerican Airlines
Deal found 6/15$401
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Sat 11/110:13 amBOS - GCM
Nonstop4h 22mJetBlue
Sat 11/153:55 pmGCM - BOS
Nonstop4h 10mJetBlue
Deal found 6/16$425
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:45 pmBDL - GCM
1 stop16h 20mAmerican Airlines
Sat 10/188:30 amGCM - BDL
1 stop13h 05mAmerican Airlines
Deal found 6/14$457
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 8/64:13 pmALB - GCM
2 stops19h 57mAmerican Airlines
Mon 8/1112:10 pmGCM - ALB
2 stops23h 01mAmerican Airlines
Deal found 6/15$488
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/299:44 amBOS - GCM
1 stop12h 36mMultiple Airlines
Tue 7/811:30 amGCM - BOS
2 stops20h 07mMultiple Airlines
Deal found 6/14$488
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/87:04 pmBOS - GCM
3 stops18h 26mUnited Airlines
Mon 7/141:35 pmGCM - BOS
2 stops20h 22mUnited Airlines
Deal found 6/14$494
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:00 pmBOS - GCM
2 stops19h 35mSouthwest
Mon 12/221:30 pmGCM - BOS
2 stops11h 15mSouthwest
Deal found 6/14$507
This Delta deal was found by Cheapflights users on 6/16. 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.
Thu 12/46:00 amBDL - GCM
1 stop6h 37mDelta
Sun 12/72:02 pmGCM - BDL
1 stop9h 44mDelta
Deal found 6/16$536
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/273:20 pmBOS - GCM
2 stops21h 00mAir Canada
Thu 10/3012:35 pmGCM - BOS
2 stops20h 03mAir Canada
Deal found 6/15$556
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 6/286:00 amALB - GCM
1 stop8h 30mUnited Airlines
Wed 7/21:35 pmGCM - ALB
2 stops33h 23mUnited Airlines
Deal found 6/16$637
This Delta deal was found by Cheapflights users on 6/15. 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.
Thu 7/36:00 amALB - GCM
1 stop6h 25mDelta
Tue 7/812:37 pmGCM - ALB
1 stop10h 14mDelta
Deal found 6/15$682

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 June 16, 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

Sun 8/17

5:35 am-11:37 am

1 stop7h 02m

George Town Owen Roberts Intl

Fri 8/29

12:50 pm-1:20 am

1 stop11h 30m

$400

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/8

7:19 pm-12:00 pm

1 stop16h 41m

George Town Owen Roberts Intl

Tue 11/11

8:30 am-4:55 pm

1 stop8h 25m

$401

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 11/1

10:13 am-1:35 pm

Nonstop4h 22m

George Town Owen Roberts Intl

Sat 11/15

3:55 pm-8:05 pm

Nonstop4h 10m

$425

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Sat 10/11

7:45 pm-11:05 am

1 stop16h 20m

George Town Owen Roberts Intl

Sat 10/18

8:30 am-10:35 pm

1 stop13h 05m

$457

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 7/29

7:04 pm-12:30 pm

3 stops18h 26m

George Town Owen Roberts Intl

Tue 8/5

1:35 pm-10:31 am

2 stops19h 56m

$464

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 6/29

9:44 am-9:20 pm

1 stop12h 36m

George Town Owen Roberts Intl

Tue 7/8

11:30 am-8:37 am

2 stops20h 07m

$488

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Wed 8/6

4:13 pm-11:10 am

2 stops19h 57m

George Town Owen Roberts Intl

Mon 8/11

12:10 pm-12:11 pm

2 stops23h 01m

$488

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 7/30

8:50 pm-11:50 am

2 stops16h 00m

George Town Owen Roberts Intl

Sun 8/3

12:45 pm-12:30 am

2 stops10h 45m

$519

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 12/4

6:00 am-12:37 pm

1 stop6h 37m

George Town Owen Roberts Intl

Sun 12/7

2:02 pm-11:46 pm

1 stop9h 44m

$536

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 10/27

3:20 pm-11:20 am

2 stops21h 00m

George Town Owen Roberts Intl

Thu 10/30

12:35 pm-9:38 am

2 stops20h 03m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 25 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 June 16, 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 June 16, 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
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,801 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,873 reviews
Southwest
8.0
Very good
4,278 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $148 on American Airlines. Other airlines that offer cheap prices include United Airlines from $235 and British Airways from $2,814 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$471FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$234Average$565FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$260Average$464FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$433FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$317Average$530FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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