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Cayman Islands

$108+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(JetBlue)

One-way from

$108
(Delta)

Popular in

February

Cheapest in

January

Average price

$421

Good round-trip deal

$310 or less

Good one-way deal

$128 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 March 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 March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. 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 4/245:15 amBOS - GCM
1 stop7h 20mAmerican Airlines
Mon 4/2812:10 pmGCM - BOS
1 stop20h 10mAmerican Airlines
Deal found 3/31$327
This United Airlines deal was found by Cheapflights users on 3/30. 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 4/236:00 amBOS - GCM
1 stop6h 45mUnited Airlines
Sun 4/271:35 pmGCM - BOS
1 stop21h 52mUnited Airlines
Deal found 3/30$328
This Delta deal was found by Cheapflights users on 3/31. 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 3/31$336
This JetBlue deal was found by Cheapflights users on 3/31. 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.
Mon 4/1410:13 amBOS - GCM
Nonstop4h 22mJetBlue
Mon 4/212:40 pmGCM - BOS
Nonstop4h 16mJetBlue
Deal found 3/31$337
This Air Canada deal was found by Cheapflights users on 3/30. 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 9/310:20 amBOS - GCM
2 stops26h 35mAir Canada
Thu 9/2512:45 pmGCM - BOS
2 stops24h 46mAir Canada
Deal found 3/30$459
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/43:40 pmBOS - GCM
2 stops46h 50mMultiple Airlines
Wed 4/911:30 amGCM - BOS
1 stop12h 15mMultiple Airlines
Deal found 3/31$465
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 5/156:00 amALB - GCM
1 stop6h 20mDelta
Tue 5/2012:35 pmGCM - ALB
1 stop10h 26mDelta
Deal found 3/30$484
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/16:14 amBDL - GCM
1 stop6h 21mAmerican Airlines
Wed 5/72:10 pmGCM - BDL
1 stop8h 03mAmerican Airlines
Deal found 3/31$484
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/17:52 pmBDL - GCM
2 stops17h 38mUnited Airlines
Wed 5/71:35 pmGCM - BDL
2 stops21h 25mUnited Airlines
Deal found 3/31$488
This American Airlines deal was found by Cheapflights users on 3/31. 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 8/304:29 pmALB - GCM
2 stops19h 21mAmerican Airlines
Sat 9/612:45 pmGCM - ALB
2 stops21h 21mAmerican Airlines
Deal found 3/31$490
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Fri 4/187:30 pmALB - GCM
1 stop20h 35mUnited Airlines
Thu 4/241:35 pmGCM - ALB
2 stops20h 01mUnited Airlines
Deal found 3/31$496
This Delta deal was found by Cheapflights users on 3/31. 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 9/266:00 amBDL - GCM
1 stop6h 31mDelta
Mon 9/2912:53 pmGCM - BDL
1 stop9h 53mDelta
Deal found 3/31$538

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 March 31, 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

Thu 4/24

5:15 am-11:35 am

1 stop7h 20m

George Town Owen Roberts Intl

Mon 4/28

12:10 pm-9:20 am

1 stop20h 10m

$327

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 4/23

6:00 am-11:45 am

1 stop6h 45m

George Town Owen Roberts Intl

Sun 4/27

1:35 pm-12:27 pm

1 stop21h 52m

$328

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

Sat 5/10

1:03 pm-10:50 pm

1 stop8h 47m

$336

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 4/14

10:13 am-1:35 pm

Nonstop4h 22m

George Town Owen Roberts Intl

Mon 4/21

2:40 pm-7:56 pm

Nonstop4h 16m

$337

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 4/4

3:40 pm-1:30 pm

2 stops46h 50m

George Town Owen Roberts Intl

Wed 4/9

11:30 am-12:45 am

1 stop12h 15m

$465

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Thu 5/15

6:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

Thu 5/22

12:35 pm-12:01 am

1 stop10h 26m

$484

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 5/1

6:14 am-11:35 am

1 stop6h 21m

George Town Owen Roberts Intl

Wed 5/7

2:10 pm-11:13 pm

1 stop8h 03m

$484

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 5/1

7:52 pm-12:30 pm

2 stops17h 38m

George Town Owen Roberts Intl

Wed 5/7

1:35 pm-12:00 pm

2 stops21h 25m

$488

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 8/30

4:29 pm-10:50 am

2 stops19h 21m

George Town Owen Roberts Intl

Sat 9/6

12:45 pm-11:06 am

2 stops21h 21m

$490

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Fri 4/18

7:30 pm-3:05 pm

1 stop20h 35m

George Town Owen Roberts Intl

Thu 4/24

1:35 pm-10:36 am

2 stops20h 01m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 26 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 March 31, 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 March 31, 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
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $108 on Delta. Other airlines that offer cheap prices include JetBlue from $113 and American Airlines from $124 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$457FlexibilityNo cancel feeOn-time67%
DeltaCheapest$252Average$479FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$263Average$473FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$284Average$459FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$324Average$514FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%
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