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Cayman Islands

$90+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$270
(United Airlines)

One-way from

$90
(Delta)

Popular in

February

Cheapest in

January

Average price

$439

Good round-trip deal

$495 or less
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, 4% 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 September 2025
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Price to beat on a round-trip 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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. 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 11/127:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Mon 11/175:45 pmGCM - BOS
1 stop18h 41mUnited Airlines
Deal found 9/11$270
This United Airlines deal was found by Cheapflights users on 9/11. 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 11/187:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Tue 11/255:45 pmGCM - BOS
2 stops15h 45mUnited Airlines
Deal found 9/11$274
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/127:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Sat 11/155:30 pmGCM - BOS
1 stop6h 12mUnited Airlines
Deal found 9/10$280
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/177:38 pmBOS - GCM
2 stops20h 52mUnited Airlines
Fri 11/215:45 pmGCM - BOS
2 stops16h 49mUnited Airlines
Deal found 9/10$284
This United Airlines deal was found by Cheapflights users on 9/10. 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 12/167:00 amBOS - GCM
1 stop9h 30mUnited Airlines
Sat 12/202:25 pmGCM - BOS
1 stop8h 23mUnited Airlines
Deal found 9/10$287
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/127:12 pmBOS - GCM
2 stops18h 18mUnited Airlines
Mon 10/274:45 pmGCM - BOS
2 stops20h 23mUnited Airlines
Deal found 9/10$291
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/265:17 pmBOS - GCM
1 stop23h 13mUnited Airlines
Wed 12/35:45 pmGCM - BOS
2 stops17h 04mUnited Airlines
Deal found 9/10$292
This United Airlines deal was found by Cheapflights users on 9/9. 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 12/154:40 pmBOS - GCM
1 stop23h 50mUnited Airlines
Fri 12/195:10 pmGCM - BOS
1 stop6h 44mUnited Airlines
Deal found 9/9$294
This United Airlines deal was found by Cheapflights users on 9/11. 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 12/46:00 amBOS - GCM
2 stops10h 30mUnited Airlines
Mon 12/85:45 pmGCM - BOS
2 stops18h 58mUnited Airlines
Deal found 9/11$295
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 12/68:20 amBOS - GCM
2 stops11h 55mAmerican Airlines
Sat 12/131:25 pmGCM - BOS
2 stops9h 50mAmerican Airlines
Deal found 9/11$302

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 September 11, 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 11/12

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Mon 11/17

5:45 pm-2:29 pm

2 stops20h 44m

$274

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 11/18

7:38 pm-4:30 pm

2 stops20h 52m

George Town Owen Roberts Intl

Tue 11/25

5:45 pm-9:30 am

2 stops15h 45m

$274

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 12/3

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sun 12/7

5:45 pm-12:21 pm

1 stop18h 36m

$280

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 12/15

6:23 pm-4:30 pm

2 stops22h 07m

George Town Owen Roberts Intl

Fri 12/19

2:25 pm-10:48 pm

1 stop8h 23m

$287

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 12/16

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sat 12/20

2:25 pm-10:48 pm

1 stop8h 23m

$287

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 1/16

6:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sun 1/18

2:25 pm-9:52 pm

1 stop7h 27m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 2/22

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Thu 2/26

2:50 pm-9:24 am

1 stop18h 34m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 12/4

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Mon 12/8

5:45 pm-12:21 pm

1 stop18h 36m

$297

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 2/22

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

Fri 2/27

2:50 pm-10:33 am

1 stop19h 43m

$301

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Sun 1/25

6:00 am-1:45 pm

1 stop7h 45m

George Town Owen Roberts Intl

Sun 2/1

2:50 pm-10:52 am

1 stop20h 02m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 20 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 September 11, 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 September 11, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 can get you from Boston to Cayman Islands in just under 9h 30m. Your travel time can differ by up to . The distance from Boston to Cayman Islands is about 1704 mi.

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

    Looking at all options, your cheapest flight can be booked for $330. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $280 on average, our data indicates $545 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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Alternative routes for Boston to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$470FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$259Average$456FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$426FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$316Average$535FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$457Average$559FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

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