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Cayman Islands

$158+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheap 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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$420
(Delta)

One-way from

$158
(Delta)

Popular in

February

Cheapest in

January

Average price

$598

Good round-trip deal

$515 or less

Good one-way deal

$348 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 Boston Logan Intl to Cayman Islands
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One-way flight from Boston Logan Intl to Cayman Islands
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Cayman Islands.
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Price to beat on a one-way flight from Boston Logan Intl to Cayman Islands.
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Find 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 April 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/28. 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 11/86:00 amBOS - GCM
2 stops10h 35mUnited Airlines
Sat 11/155:45 pmGCM - BOS
2 stops16h 24mUnited Airlines
Deal found 4/28$420
This JetBlue deal was found by Cheapflights users on 4/29. 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.
Sat 11/110:13 amBOS - GCM
Nonstop4h 22mJetBlue
Sat 11/83:55 pmGCM - BOS
Nonstop4h 10mJetBlue
Deal found 4/29$425
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/155:00 amBOS - GCM
1 stop7h 20mAmerican Airlines
Wed 5/2112:25 pmGCM - BOS
2 stops9h 26mAmerican Airlines
Deal found 4/28$431
This Priceline deal was found by Cheapflights users on 4/29. 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.
Sun 6/155:50 amBOS - GCM
2 stops31h 05mAir Canada
Thu 6/1912:50 pmGCM - BOS
2 stops19h 45mAir Canada
Deal found 4/29$434
This Southwest deal was found by Cheapflights users on 4/29. 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.
Sat 5/107:30 amBOS - GCM
1 stop5h 45mSouthwest
Sat 5/171:10 pmGCM - BOS
1 stop9h 15mSouthwest
Deal found 4/29$460
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:40 amBOS - GCM
1 stop6h 42mDelta
Sat 5/101:03 pmGCM - BOS
1 stop8h 47mDelta
Deal found 4/27$480
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Wed 6/1110:20 amBOS - GCM
2 stops26h 35mMultiple Airlines
Wed 6/1811:30 amGCM - BOS
3 stops34h 49mMultiple Airlines
Deal found 4/29$556
This flugladen.de deal was found by Cheapflights users on 4/28. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:21 amBOS - GCM
1 stop6h 49mIberia
Fri 6/2012:10 pmGCM - BOS
1 stop11h 25mIberia
Deal found 4/28$589
This FlightHub deal was found by Cheapflights users on 4/29. 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.
Wed 6/47:00 pmBOS - CYB
2 stops21h 25mMultiple Airlines
Sun 6/87:25 pmCYB - BOS
2 stops37h 30mMultiple Airlines
Deal found 4/29$790

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 April 29, 2025.
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 5/14

5:40 am-11:20 am

1 stop6h 40m

George Town Owen Roberts Intl

Wed 6/11

12:40 pm-10:43 pm

1 stop9h 03m

$420

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 7/25

8:20 pm-1:30 pm

1 stop18h 10m

George Town Owen Roberts Intl

Mon 7/28

1:35 pm-10:31 am

2 stops19h 56m

$424

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 5/15

5:00 am-11:20 am

1 stop7h 20m

George Town Owen Roberts Intl

Wed 5/21

12:25 pm-10:51 pm

2 stops9h 26m

$431

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 6/15

5:50 am-11:55 am

2 stops31h 05m

George Town Owen Roberts Intl

Thu 6/19

12:50 pm-9:35 am

2 stops19h 45m

$434

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sat 5/10

7:30 am-12:15 pm

1 stop5h 45m

George Town Owen Roberts Intl

Sat 5/17

1:10 pm-11:25 pm

1 stop9h 15m

$460

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 6/1

9:46 am-11:40 am

1 stop26h 54m

George Town Owen Roberts Intl

Sat 6/14

11:25 am-12:44 am

1 stop12h 19m

$527

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 6/13

7:21 am-1:10 pm

1 stop6h 49m

George Town Owen Roberts Intl

Fri 6/20

12:10 pm-12:35 am

1 stop11h 25m

$589

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Wed 6/4

7:00 pm-3:25 pm

2 stops21h 25m

Cayman Brac Gerrard-Smith

Sun 6/8

7:25 pm-9:55 am

2 stops37h 30m

$790

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 7/8

5:30 pm-4:10 pm

3 stops23h 40m

George Town Owen Roberts Intl

Mon 7/14

6:05 pm-5:10 pm

2 stops22h 05m

$8,446

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 5/11

5:40 am-11:20 am

1 stop6h 40m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 17 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 $467). Flying from Boston 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 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 April 29, 2025.

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 April 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Boston to Cayman Islands to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $158. Users have also found prices from $163 and $183 on Air Canada and JetBlue, respectively.

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

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $419 on average our data indicates $439 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 $467). Flying from Boston 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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Top 6 airlines flying from Boston to Cayman Islands

Discover the top 6 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
DeltaCheapest$252Average$446FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$262Average$473FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$454FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$320Average$524FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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