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Cayman Islands

$68+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Find cheap flights from Massachusetts to Cayman Islands with Cheapflights

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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 November 21, 2024.

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 November 21, 2024.

This JetBlue deal was found by Cheapflights users on 11/19. 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.
Wed 12/1110:00 amBOS - GCM
Nonstop4h 18mJetBlue
Mon 12/163:18 pmGCM - BOS
Nonstop4h 02mJetBlue
Deal found 11/19$284
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 12/115:25 amBOS - GCM
1 stop7h 17mDelta
Mon 12/161:57 pmGCM - BOS
1 stop9h 47mDelta
Deal found 11/19$298
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Wed 12/115:56 pmBOS - GCM
2 stops18h 04mAmerican Airlines
Tue 12/171:40 pmGCM - BOS
2 stops9h 05mAmerican Airlines
Deal found 11/20$303
This United deal was found by Cheapflights users on 11/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/187:38 pmBOS - GCM
2 stops18h 07mUnited Airlines
Mon 12/232:50 pmGCM - BOS
2 stops19h 10mUnited Airlines
Deal found 11/20$393
This Air Canada deal was found by Cheapflights users on 11/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/305:35 pmBOS - GCM
2 stops21h 25mAir Canada
Thu 12/52:40 pmGCM - BOS
2 stops19h 28mAir Canada
Deal found 11/20$479
This American Airlines deal was found by Cheapflights users on 11/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/137:36 pmBDL - GCM
1 stop17h 04mAmerican Airlines
Wed 12/183:30 pmGCM - BDL
1 stop8h 11mAmerican Airlines
Deal found 11/21$483
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/196:00 amALB - GCM
1 stop6h 33mDelta
Sun 12/291:52 pmGCM - ALB
1 stop10h 01mDelta
Deal found 11/21$526
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1210:34 amBOS - GCM
3 stops25h 06mMultiple Airlines
Thu 12/194:00 pmGCM - BOS
2 stops18h 08mMultiple Airlines
Deal found 11/19$539
This Southwest deal was found by Cheapflights users on 11/20. 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.
Mon 12/210:35 pmBOS - GCM
2 stops14h 20mSouthwest
Mon 12/91:50 pmGCM - BOS
2 stops8h 35mSouthwest
Deal found 11/20$586
This American Airlines deal was found by Cheapflights users on 11/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/192:42 pmALB - GCM
2 stops21h 18mAmerican Airlines
Sun 12/295:15 pmGCM - ALB
2 stops18h 31mAmerican Airlines
Deal found 11/21$647
This United Airlines deal was found by Cheapflights users on 11/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:00 amBDL - GCM
2 stops10h 25mUnited Airlines
Wed 12/185:35 pmGCM - BDL
3 stops30h 24mUnited Airlines
Deal found 11/21$909
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/216:30 amBOS - CYB
1 stop6h 50mMultiple Airlines
Sun 12/2910:55 amCYB - BOS
2 stops22h 04mMultiple Airlines
Deal found 11/20$941

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 1/6

10:40 am-3:09 pm

Nonstop4h 29m

George Town Owen Roberts Intl

Sat 1/11

3:40 pm-7:40 pm

Nonstop4h 00m

$259

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 1/22

5:40 am-12:44 pm

1 stop7h 04m

George Town Owen Roberts Intl

Fri 1/24

2:09 pm-12:58 am

1 stop10h 49m

$290

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 1/23

6:39 pm-12:35 pm

1 stop17h 56m

George Town Owen Roberts Intl

Mon 1/27

3:35 pm-3:54 pm

1 stop24h 19m

$299

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 1/6

6:05 am-1:15 pm

1 stop7h 10m

George Town Owen Roberts Intl

Sat 1/11

5:45 pm-11:59 pm

1 stop6h 14m

$388

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Wed 2/19

6:06 am-12:44 pm

1 stop6h 38m

George Town Owen Roberts Intl

Tue 2/25

2:09 pm-10:38 pm

1 stop8h 29m

$440

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Mon 1/13

6:05 am-12:44 pm

1 stop6h 39m

George Town Owen Roberts Intl

Thu 1/16

2:09 pm-11:56 pm

1 stop9h 47m

$440

AlbanyGeorge Town

ALB - GCM

ALBGCM

Albany Intl

Sat 2/8

5:21 pm-2:30 pm

2 stops21h 09m

George Town Owen Roberts Intl

Tue 2/18

3:20 pm-12:14 am

1 stop8h 54m

$445

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Mon 1/13

5:19 pm-12:35 pm

2 stops19h 16m

George Town Owen Roberts Intl

Thu 1/16

1:40 pm-10:43 pm

1 stop9h 03m

$445

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 1/20

6:00 am-4:10 pm

2 stops10h 10m

George Town Owen Roberts Intl

Wed 1/29

11:30 am-9:34 am

1 stop22h 04m

$464

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 1/11

3:40 pm-3:00 pm

2 stops23h 20m

George Town Owen Roberts Intl

Sun 1/19

4:00 pm-12:12 pm

1 stop20h 12m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 30 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 June is currently the most expensive (average of $560). 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 November 21, 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 November 21, 2024.
Read reviews from past customers who have flown JetBlue, Delta and American 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
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,389 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $68 on JetBlue. Other airlines that offer cheap prices include Delta from $97 and American Airlines from $117 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 June is currently the most expensive (average of $560). 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 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$260Average$568FlexibilityNo cancel feeOn-time62%
DeltaCheapest$287Average$429FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$289Average$500FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$293Average$474FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$343Average$417FlexibilityNo cancel feeOn-time67%
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