Cayman Islands

$83+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Feb 28 — Mar 71
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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 January 29, 2026.

This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:27 am
BOS
-
GCM
1 stop8h 16m
Spirit Airlines
Thu 2/262:49 pm
GCM
-
BOS
1 stop8h 55m
Spirit Airlines
Deal found 1/27$276
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 2/186:30 am
BOS
-
GCM
1 stop8h 05m
American Airlines
Tue 2/243:35 pm
GCM
-
BOS
1 stop8h 24m
American Airlines
Deal found 1/27$285
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/189:00 am
BOS
-
GCM
2 stops11h 15m
American Airlines
Wed 3/2512:05 pm
GCM
-
BOS
2 stops9h 35m
American Airlines
Deal found 1/27$290
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/215:40 am
BOS
-
GCM
1 stop7h 40m
Spirit Airlines
Sat 3/281:15 pm
GCM
-
BOS
1 stop9h 44m
Spirit Airlines
Deal found 1/27$307
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:40 am
BOS
-
GCM
1 stop7h 40m
Spirit Airlines
Sat 4/181:40 pm
GCM
-
BOS
1 stop9h 19m
Spirit Airlines
Deal found 1/26$311
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/287:19 pm
BOS
-
GCM
2 stops18h 26m
United Airlines
Wed 3/42:25 pm
GCM
-
BOS
1 stop7h 26m
United Airlines
Deal found 1/27$318
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/256:00 am
BOS
-
GCM
1 stop7h 45m
United Airlines
Wed 4/112:55 pm
GCM
-
BOS
1 stop7h 59m
United Airlines
Deal found 1/27$321
This Booking.com deal was found by Cheapflights users on 1/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:15 am
BOS
-
GCM
1 stop29h 10m
Multiple Airlines
Thu 3/121:52 pm
GCM
-
BOS
1 stop9h 07m
Multiple Airlines
Deal found 1/26$332
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:40 am
BOS
-
GCM
1 stop7h 40m
Spirit Airlines
Thu 3/191:52 pm
GCM
-
BOS
1 stop9h 07m
Spirit Airlines
Deal found 1/27$335
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/57:40 am
BOS
-
GCM
1 stop6h 34m
American Airlines
Sun 3/82:44 pm
GCM
-
BOS
1 stop8h 21m
American Airlines
Deal found 1/27$340
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 1/307:07 pm
BOS
-
GCM
2 stops18h 38m
United Airlines
Sun 2/12:25 pm
GCM
-
BOS
1 stop7h 27m
United Airlines
Deal found 1/27$341

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Booking.com)

One-way from

$83
(FlightHub)

Popular in

December

Cheapest in

March

Average price

$408

Good round-trip deal

$414 or less

Good one-way deal

$164 or less
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
From Boston Logan Intl to Cayman Islands
One-way flight from Boston Logan Intl to Cayman Islands
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in January 2026
Price to beat on a round-trip flight from Boston Logan Intl to Cayman Islands.
Price to beat on a one-way flight from Boston Logan Intl to Cayman Islands.

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 January 29, 2026.
Use the filters below to find and compare flights from Boston to the Cayman Islands that are best for you.

Fly from

Boston

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/25

6:00 am-12:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Wed 4/1

12:55 pm-9:54 pm

1 stop7h 59m

$321

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 2/28

7:19 pm-1:15 pm

2 stops17h 56m

George Town Owen Roberts Intl

Wed 3/4

2:25 pm-9:58 am

2 stops19h 33m

$343

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 6/13

5:10 am-11:30 am

1 stop7h 20m

George Town Owen Roberts Intl

Sat 6/20

12:25 pm-9:53 am

1 stop20h 28m

$365

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 2/23

5:47 am-12:08 pm

1 stop6h 21m

George Town Owen Roberts Intl

Sun 3/1

3:35 pm-11:59 pm

1 stop8h 24m

$376

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 3/6

6:30 pm-1:45 pm

2 stops19h 15m

George Town Owen Roberts Intl

Wed 3/11

1:25 pm-11:57 pm

2 stops9h 32m

$378

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 4/19

6:45 pm-11:10 am

1 stop17h 25m

George Town Owen Roberts Intl

Tue 4/21

1:55 pm-7:17 am

2 stops16h 22m

$389

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/18

5:35 am-11:47 am

1 stop7h 12m

George Town Owen Roberts Intl

Sat 3/21

1:00 pm-10:54 pm

1 stop8h 54m

$391

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 4/19

8:50 pm-12:00 pm

1 stop16h 10m

George Town Owen Roberts Intl

Tue 4/28

1:25 pm-11:58 pm

1 stop9h 33m

$391

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 4/14

5:40 am-12:00 pm

1 stop7h 20m

George Town Owen Roberts Intl

Wed 4/22

1:25 pm-1:15 am

1 stop10h 50m

$391

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 3/6

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Sun 3/8

4:45 pm-12:49 pm

2 stops19h 04m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 19 results
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 January 29, 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 January 29, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines 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.

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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.

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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.

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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.

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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.

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

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, Air Canada, and American Airlines can get you from Boston to Cayman Islands in just under 6h 21m. Your travel time can differ by up to 1h 24m. 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 $103 on United Airlines and JetBlue, respectively.

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

    Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $291 on average, our data indicates $342 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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Alternative routes for Boston to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$72Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$190Average$380FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$281Average$507FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$382Average$545FlexibilityNo cancel feeOn-time71%

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