Cayman Islands

$98+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Dec 27 — Jan 31
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Cheap flight deals from Massachusetts to Cayman Islands

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$294
(JetBlue Airways)

One-way from

$98
(JetBlue)
From Massachusetts to Cayman Islands
One-way flight from Massachusetts to Cayman Islands

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 December 22, 2024.

This American Airlines deal was found by Cheapflights users on 12/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/296:39 pmBOS - GCM
1 stop21h 41mAmerican Airlines
Thu 1/91:40 pmGCM - BOS
1 stop7h 12mAmerican Airlines
Deal found 12/22$479
This JetBlue deal was found by Cheapflights users on 12/21. 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.
Wed 12/2510:40 amBOS - GCM
Nonstop4h 29mJetBlue
Wed 1/14:10 pmGCM - BOS
Nonstop4h 00mJetBlue
Deal found 12/21$499
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Thu 12/265:45 amBOS - GCM
1 stop10h 45mUnited Airlines
Tue 12/315:35 pmGCM - BOS
1 stop16h 25mUnited Airlines
Deal found 12/22$513
This Delta deal was found by Cheapflights users on 12/22. 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.
Wed 12/255:40 amBOS - GCM
1 stop8h 52mDelta
Wed 1/13:47 pmGCM - BOS
1 stop9h 03mDelta
Deal found 12/22$548
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/316:17 pmBOS - GCM
1 stop21h 53mMultiple Airlines
Tue 1/711:30 amGCM - BOS
1 stop21h 29mMultiple Airlines
Deal found 12/21$580
This Southwest deal was found by Cheapflights users on 12/21. 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.
Sun 12/228:00 pmBOS - GCM
2 stops16h 55mSouthwest
Wed 12/251:50 pmGCM - BOS
2 stops8h 35mSouthwest
Deal found 12/21$736
This Southwest deal was found by Cheapflights users on 12/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/295:05 amBDL - GCM
1 stop7h 50mSouthwest
Fri 1/31:50 pmGCM - BDL
2 stops10h 00mSouthwest
Deal found 12/22$909
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:30 pmBOS - CYB
2 stops22h 20mMultiple Airlines
Sat 12/283:55 pmCYB - BOS
2 stops41h 47mMultiple Airlines
Deal found 12/21$1,184
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Sun 12/296:15 pmBDL - GCM
2 stops46h 15mUnited Airlines
Fri 1/35:35 pmGCM - BDL
3 stops30h 24mUnited Airlines
Deal found 12/22$1,342
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/298:05 amBDL - GCM
3 stops29h 35mMultiple Airlines
Fri 1/34:45 pmGCM - BDL
3 stops29h 57mMultiple Airlines
Deal found 12/22$2,779
This KAYAK deal was found by Cheapflights users on 12/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:25 pmBOS - GCM
3 stops45h 30mBritish Airways
Mon 1/66:50 pmGCM - BOS
3 stops46h 00mBritish Airways
Deal found 12/21$9,669

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 2/26

9:03 am-1:32 pm

Nonstop4h 29m

George Town Owen Roberts Intl

Wed 3/5

2:37 pm-6:45 pm

Nonstop4h 08m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/11

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sat 1/18

5:45 pm-11:59 pm

1 stop6h 14m

$308

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/11

6:00 am-2:00 pm

1 stop8h 00m

George Town Owen Roberts Intl

Sat 1/18

1:10 pm-8:39 pm

1 stop7h 29m

$310

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 3/14

6:10 am-2:00 pm

1 stop8h 50m

George Town Owen Roberts Intl

Fri 3/21

3:00 pm-12:12 pm

1 stop20h 12m

$427

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 2/19

8:09 pm-9:20 pm

1 stop25h 11m

George Town Owen Roberts Intl

Tue 3/4

11:30 am-7:14 pm

1 stop7h 44m

$449

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 4/10

9:45 pm-11:50 am

2 stops15h 05m

George Town Owen Roberts Intl

Tue 4/15

12:45 pm-10:25 pm

2 stops8h 40m

$523

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Mon 3/3

6:06 am-12:38 pm

1 stop6h 32m

George Town Owen Roberts Intl

Sat 3/8

3:19 pm-10:40 pm

1 stop7h 21m

$526

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Thu 2/20

6:10 am-12:38 pm

1 stop6h 28m

George Town Owen Roberts Intl

Mon 3/3

2:04 pm-9:08 pm

1 stop7h 04m

$526

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sun 1/19

5:15 pm-2:30 pm

2 stops21h 15m

George Town Owen Roberts Intl

Sun 1/26

3:35 pm-12:14 pm

2 stops20h 39m

$531

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Sat 1/25

5:25 pm-2:30 pm

2 stops21h 05m

George Town Owen Roberts Intl

Thu 1/30

3:35 pm-11:58 pm

1 stop8h 23m

$531

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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.

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 December 22, 2024.

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 December 22, 2024.
Read reviews from past customers who have flown American Airlines, JetBlue 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.
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,265 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.2
Good
10,000 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.7

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $98 on JetBlue. Other airlines that offer cheap prices include Delta from $102 and American Airlines from $103 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.

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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.

Top 5 airlines flying from Massachusetts to Cayman Islands

Discover the top 5 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$261Average$540FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$279Average$487FlexibilityNo cancel feeOn-time69%
DeltaCheapest$287Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$499FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$343Average$419FlexibilityNo cancel feeOn-time67%
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