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$89+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(United Airlines)

One-way from

$89
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$598

Good round-trip deal

$320 or less

Good one-way deal

$103 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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Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. 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.
mié. 3/127:36 pmBOS - GCM
2 stops17h 39mUnited Airlines
mar. 3/184:25 pmGCM - BOS
2 stops17h 34mUnited Airlines
Deal found 2/19$294
This American Airlines deal was found by Cheapflights users on 2/19. 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.
mié. 3/197:11 amBOS - GCM
1 stop8h 23mAmerican Airlines
mié. 3/2612:45 pmGCM - BOS
2 stops8h 58mAmerican Airlines
Deal found 2/19$296
This Delta deal was found by Cheapflights users on 2/19. 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.
jue. 3/205:40 amBOS - GCM
1 stop6h 58mDelta
lun. 3/241:03 pmGCM - BOS
1 stop11h 02mDelta
Deal found 2/19$330
This JetBlue deal was found by Cheapflights users on 2/19. 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.
mié. 3/125:20 amBOS - GCM
1 stop6h 50mJetBlue
mié. 3/191:52 pmGCM - BOS
Nonstop4h 07mJetBlue
Deal found 2/19$331
This Air Canada deal was found by Cheapflights users on 2/18. 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.
jue. 5/16:00 amBOS - GCM
1 stop6h 55mAir Canada
lun. 5/512:50 pmGCM - BOS
2 stops24h 42mAir Canada
Deal found 2/18$425
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
mar. 3/411:33 amBOS - GCM
1 stop28h 37mMultiple Airlines
dom. 3/92:00 pmGCM - BOS
1 stop17h 52mMultiple Airlines
Deal found 2/18$451
This United Airlines deal was found by Cheapflights users on 2/20. 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.
mié. 4/302:56 pmBDL - GCM
2 stops22h 34mUnited Airlines
sáb. 5/34:15 pmGCM - BDL
1 stop16h 20mUnited Airlines
Deal found 2/20$524
This American Airlines deal was found by Cheapflights users on 2/20. 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.
mié. 4/305:02 amBDL - GCM
2 stops8h 57mAmerican Airlines
sáb. 5/312:25 pmGCM - BDL
2 stops19h 37mAmerican Airlines
Deal found 2/20$528
This United Airlines deal was found by Cheapflights users on 2/19. 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. 4/56:00 amALB - GCM
1 stop10h 10mUnited Airlines
sáb. 4/124:15 pmGCM - ALB
1 stop16h 50mUnited Airlines
Deal found 2/19$538
This American Airlines deal was found by Cheapflights users on 2/20. 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.
jue. 7/177:47 pmALB - GCM
1 stop16h 18mAmerican Airlines
jue. 7/313:50 pmGCM - ALB
2 stops18h 01mAmerican Airlines
Deal found 2/20$553
This Southwest deal was found by Cheapflights users on 2/20. 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.
mar. 5/277:05 amBDL - GCM
1 stop5h 45mSouthwest
dom. 6/112:45 pmGCM - BDL
2 stops10h 20mSouthwest
Deal found 2/20$576
This American Airlines deal was found by Cheapflights users on 2/19. 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.
lun. 3/172:12 pmORH - GCM
2 stops22h 33mAmerican Airlines
mar. 3/2512:45 pmGCM - ORH
2 stops23h 55mAmerican Airlines
Deal found 2/19$580

Find flights from Massachusetts to Cayman Islands within your budget

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 febrero 20, 2025.

Fly from

Massachusetts

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mié. 3/12

7:36 pm-12:15 pm

2 stops17h 39m

George Town Owen Roberts Intl

mar. 3/18

4:25 pm-10:59 am

2 stops17h 34m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mié. 3/19

7:11 am-2:34 pm

1 stop8h 23m

George Town Owen Roberts Intl

mié. 3/26

12:45 pm-10:43 pm

2 stops8h 58m

$296

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

lun. 3/10

9:47 am-1:16 pm

Nonstop4h 29m

George Town Owen Roberts Intl

mié. 3/19

1:52 pm-6:59 pm

Nonstop4h 07m

$316

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

jue. 3/20

5:40 am-11:38 am

1 stop6h 58m

George Town Owen Roberts Intl

mar. 3/25

1:03 pm-1:05 am

1 stop11h 02m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

jue. 5/1

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

lun. 5/5

12:50 pm-10:03 am

1 stop20h 13m

$425

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mar. 3/4

11:33 am-4:10 pm

1 stop28h 37m

George Town Owen Roberts Intl

dom. 3/9

2:00 pm-8:52 am

1 stop17h 52m

$451

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

mié. 4/30

2:56 pm-12:30 pm

2 stops22h 34m

George Town Owen Roberts Intl

sáb. 5/3

4:15 pm-9:35 am

1 stop16h 20m

$524

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

mié. 4/30

5:02 am-12:59 pm

2 stops8h 57m

George Town Owen Roberts Intl

sáb. 5/3

12:25 pm-9:02 am

2 stops19h 37m

$528

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

sáb. 4/5

6:00 am-3:10 pm

1 stop10h 10m

George Town Owen Roberts Intl

sáb. 4/12

4:15 pm-10:05 am

1 stop16h 50m

$538

WorcesterGeorge Town

ORH - GCM

ORHGCM

Worcester

lun. 3/17

2:12 pm-11:45 am

2 stops22h 33m

George Town Owen Roberts Intl

mar. 3/25

12:45 pm-1:40 pm

2 stops23h 55m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Massachusetts to Cayman Islands

Get recent, data-driven insights about flights from Massachusetts to Cayman Islands including ideal travel times, pricing trends, and more.

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 febrero 20, 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 febrero 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and JetBlue 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
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $89 on JetBlue. Other airlines that offer cheap prices include American Airlines from $94 and Delta from $104 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$261Average$487FlexibilityNo cancel feeOn-time62%
DeltaCheapest$288Average$435FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$291Average$464FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$325Average$508FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$618Average$934FlexibilityNo cancel feeOn-time63%
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