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Cayman Islands

$94+ Cheap flights from Boston (BOS) 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap flight deals from Boston to Cayman Islands

Cheapest flights from Boston to Cayman Islands
Explore the most affordable flight options available from Boston to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 27, 2026.

This American Airlines deal was found by Cheapflights users on 3/25. 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.
Tue 4/78:30 pm
BOS
-
GCM
2 stops16h 01m
American Airlines
Tue 4/1412:35 pm
GCM
-
BOS
1 stop7h 01m
American Airlines
Deal found 3/25$321
This American Airlines deal was found by Cheapflights users on 3/22. 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.
Fri 4/36:52 am
BOS
-
GCM
1 stop7h 52m
American Airlines
Mon 4/62:44 pm
GCM
-
BOS
1 stop8h 27m
American Airlines
Deal found 3/22$326
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/25:30 am
BOS
-
GCM
1 stop10h 30m
American Airlines
Mon 4/62:44 pm
GCM
-
BOS
1 stop8h 27m
American Airlines
Deal found 3/27$335
This United Airlines deal was found by Cheapflights users on 3/27. 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 5/127:27 pm
BOS
-
GCM
2 stops18h 03m
United Airlines
Tue 5/191:35 pm
GCM
-
BOS
2 stops18h 50m
United Airlines
Deal found 3/27$344
This Expedia deal was found by Cheapflights users on 3/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:55 pm
BOS
-
GCM
1 stop17h 30m
Air Canada
Thu 6/1812:25 pm
GCM
-
BOS
1 stop9h 13m
Air Canada
Deal found 3/27$345
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/36:25 pm
BOS
-
GCM
2 stops19h 05m
United Airlines
Sun 4/51:35 pm
GCM
-
BOS
1 stop9h 05m
United Airlines
Deal found 3/26$351
This United Airlines deal was found by Cheapflights users on 3/24. 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 11/117:40 am
BOS
-
GCM
1 stop8h 50m
United Airlines
Mon 11/165:45 pm
GCM
-
BOS
1 stop18h 50m
United Airlines
Deal found 3/24$352
This American Airlines deal was found by Cheapflights users on 3/25. 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 3/275:47 am
BOS
-
GCM
1 stop8h 26m
American Airlines
Fri 4/32:44 pm
GCM
-
BOS
1 stop8h 27m
American Airlines
Deal found 3/25$353
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Mon 4/276:00 am
BOS
-
GCM
1 stop6h 45m
United Airlines
Sat 5/21:50 pm
GCM
-
BOS
1 stop10h 09m
United Airlines
Deal found 3/23$360
This Expedia deal was found by Cheapflights users on 3/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:50 am
BOS
-
CYB
2 stops29h 35m
Multiple Airlines
Sun 8/303:55 pm
CYB
-
BOS
2 stops29h 43m
Multiple Airlines
Deal found 3/26$730

Find flight deals from Boston to Cayman Islands

Keep the following information in mind while searching for Boston to Cayman Islands flight deals. Data was last updated March 27, 2026.

Round-trip from

$321
(American Airlines)

One-way from

$94
(Delta)

Popular in

December

Cheapest in

January

Average price

$426

Good one-way deal

$188 or less
From Boston Logan Intl to Cayman Islands
Search Deals
One-way flight from Boston Logan Intl to Cayman Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Cayman Islands.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 27, 2026.
Use the filters below to find and compare flights from Boston to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 4/15

6:00 am-11:45 am

1 stop6h 45m

George Town Owen Roberts Intl

Sun 4/19

2:45 pm-10:04 am

2 stops18h 19m

$389

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 4/28

5:35 am-12:00 pm

1 stop7h 25m

George Town Owen Roberts Intl

Fri 5/1

1:25 pm-1:22 am

1 stop10h 57m

$412

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 4/27

5:35 am-12:00 pm

1 stop7h 25m

George Town Owen Roberts Intl

Fri 5/1

1:25 pm-1:22 am

1 stop10h 57m

$412

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 4/23

6:00 am-12:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sun 4/26

1:50 pm-1:29 pm

2 stops22h 39m

$444

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 6/1

5:44 pm-12:30 pm

2 stops19h 46m

George Town Owen Roberts Intl

Sat 6/13

4:15 pm-11:16 am

2 stops18h 01m

$444

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 5/26

8:15 am-12:30 pm

2 stops29h 15m

George Town Owen Roberts Intl

Sat 5/30

4:15 pm-11:16 am

2 stops18h 01m

$444

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 4/27

8:15 am-12:45 pm

1 stop29h 30m

George Town Owen Roberts Intl

Fri 5/1

1:35 pm-5:22 pm

2 stops26h 47m

$455
Quickest round-trip

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 8/17

5:45 am-11:41 am

1 stop6h 56m

George Town Owen Roberts Intl

Mon 8/24

12:56 pm-1:06 am

1 stop11h 10m

$477

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 4/27

6:00 am-11:45 am

1 stop6h 45m

George Town Owen Roberts Intl

Sat 5/2

1:50 pm-11:01 am

1 stop20h 11m

$482

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Sun 8/23

10:50 am-3:25 pm

2 stops29h 35m

Cayman Brac Gerrard-Smith

Sun 8/30

3:55 pm-10:38 pm

2 stops29h 43m

$730

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Best time to book a flight from Boston to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Boston 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 Boston to the Cayman Islands

What is the cheapest month to book a flight from Boston to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $72). Flying from Boston to Cayman Islands in August is currently the most expensive (average of $404). 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 BOS to KY?

Find hourly flight availability from Boston 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 27, 2026.

When flying from Boston 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 27, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue from Boston to the Cayman Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,340 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,340 reviews
Delta
7.9
Good
8,340 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,491 reviews
Delta
7.9
Good
8,340 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,340 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,507 reviews
Delta
7.9
Good
8,340 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Crew

8.5

Food

7.2

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Boston 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 airport do you fly from for flights from Boston to Cayman Islands?

    Boston Logan Intl (BOS), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Boston to Cayman Islands.

  • How long is the flight from Boston to Cayman Islands?

    United Airlines and Delta can get you from Boston to Cayman Islands in just under 6h 45m. Your travel time can differ by up to 40m. The distance from Boston to Cayman Islands is about 1704 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Boston to Cayman Islands one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $54. Users have also found prices from $90 and $108 on United Airlines and American Airlines, respectively.

  • What are the cheapest flights from Boston to Cayman Islands?

    Looking at all options, your cheapest flight can be booked for $144. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $285 on average, our data indicates $188 when flying from Boston to Cayman Islands.

  • Can I find deals for flights from Boston to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Boston to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Cayman Islands.

  • Can I find deals for business class flights from Boston to Cayman Islands?

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $72). Flying from Boston to Cayman Islands in August is currently the most expensive (average of $404). 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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Top 4 airlines flying from Boston to Cayman Islands

Discover the top 4 airlines that operate flights from Boston 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$72Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$193Average$409FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$315Average$531FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$351Average$527FlexibilityNo cancel feeOn-time71%

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