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$183+ Cheap flights from the Cayman Islands to Boston (BOS)

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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from Cayman Islands to Boston

Cheapest flights from Cayman Islands to Boston
Explore the most affordable flight options available from Cayman Islands to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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 11/75:45 pmGCM - BOS
2 stops22h 35mUnited Airlines
Tue 11/116:00 amBOS - GCM
2 stops10h 30mUnited Airlines
Deal found 10/27$275
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/115:45 pmGCM - BOS
2 stops23h 30mUnited Airlines
Sun 12/146:00 amBOS - GCM
1 stop7h 15mUnited Airlines
Deal found 10/27$308
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/62:00 pmGCM - BOS
1 stop11h 13mDelta
Sun 11/95:40 amBOS - GCM
1 stop6h 55mDelta
Deal found 10/27$311
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/65:45 pmGCM - BOS
1 stop27h 50mUnited Airlines
Sun 11/95:30 amBOS - GCM
2 stops11h 00mUnited Airlines
Deal found 10/27$329
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:10 pmGCM - BOS
1 stop7h 10mAmerican Airlines
Sun 11/95:25 amBOS - GCM
1 stop8h 49mAmerican Airlines
Deal found 10/26$353
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/113:45 pmGCM - BOS
2 stops15h 36mAmerican Airlines
Sun 12/146:00 amBOS - GCM
2 stops8h 44mAmerican Airlines
Deal found 10/27$400
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:45 pmGCM - BOS
1 stop29h 30mUnited Airlines
Sun 11/306:05 amBOS - GCM
1 stop7h 10mUnited Airlines
Deal found 10/29$413
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/75:45 pmGCM - BOS
3 stops24h 47mUnited Airlines
Sun 11/97:38 pmBOS - GCM
2 stops20h 52mUnited Airlines
Deal found 10/26$638
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:00 amGCM - BOS
3 stops29h 20mMultiple Airlines
Sun 11/309:54 pmBOS - GCM
2 stops23h 21mMultiple Airlines
Deal found 10/27$728

Cheap flight deals from Cayman Islands to Boston

Keep the following information in mind while searching for Cayman Islands to Boston flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$308
(United Airlines)

One-way from

$183
(United Airlines)

Popular in

June

Cheapest in

November

Average price

$535

Good round-trip deal

$919 or less

Good one-way deal

$250 or less
Provider with most accurate pricing for George Town Owen Roberts Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for George Town Owen Roberts Intl-Boston Logan Intl flights.
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From Cayman Islands to Boston Logan Intl
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One-way flight from Cayman Islands to Boston Logan Intl
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Highest demand for flights based on searches. 20% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Cayman Islands to Boston Logan Intl.
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Price to beat on a one-way flight from Cayman Islands to Boston Logan Intl.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Boston 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 October 29, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Boston that are best for you.

Fly from

Cayman Islands

Fly to

Boston

Route

Depart

Return

Price

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/11

5:45 pm-5:15 pm

2 stops23h 30m

Boston Logan Intl

Sun 12/14

6:00 am-1:15 pm

1 stop7h 15m

$308

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/11

1:50 pm-1:27 am

1 stop11h 37m

Boston Logan Intl

Sun 12/14

5:40 am-12:35 pm

1 stop6h 55m

$311

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/11

3:45 pm-7:21 am

2 stops15h 36m

Boston Logan Intl

Sun 12/14

6:00 am-2:44 pm

2 stops8h 44m

$400

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 4/18

1:30 pm-6:40 pm

Nonstop4h 10m

Boston Logan Intl

Sat 4/25

11:10 am-2:32 pm

Nonstop4h 22m

$426

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Tue 3/17

12:30 pm-9:57 am

1 stop20h 27m

Boston Logan Intl

Wed 3/18

1:00 pm-11:25 am

1 stop23h 25m

$454

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Tue 3/17

2:10 pm-12:14 am

1 stop9h 04m

Boston Logan Intl

Wed 3/18

5:30 am-1:02 pm

1 stop8h 32m

$474

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 4/18

3:15 pm-10:23 am

1 stop18h 08m

Boston Logan Intl

Sat 4/25

6:00 am-11:00 am

1 stop6h 00m

$526

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Thu 12/25

5:10 pm-11:54 pm

1 stop6h 44m

$183

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Wed 12/24

2:50 pm-11:54 pm

2 stops33h 04m

$189

George TownBoston

GCM - BOS

GCMBOS

George Town Owen Roberts Intl

Sat 2/14

5:45 pm-12:46 pm

2 stops19h 01m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 17 results
1
2

Best time to book a flight from Cayman Islands to Boston

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

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

Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Boston (average of $206). Flying from Cayman Islands to Boston in May is currently the most expensive (average of $460). 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.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated October 29, 2025.
Peruse reviews from past customers who have flown with American Airlines and JetBlue from the Cayman Islands to Boston 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.
American Airlines
7.2
Good
11,032 reviews

Overall

7.2

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,032 reviews
American Airlines
7.2
Good
11,032 reviews

Overall

7.2

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
JetBlue
7.2
Good
2,907 reviews
American Airlines
7.2
Good
11,032 reviews

Overall

7.2

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Boston. 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 into for flights to Boston from Cayman Islands?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Cayman Islands. Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    United Airlines, Delta, and American Airlines can get you from Cayman Islands to Boston in just under 11h 37m. Your travel time can differ by up to 11h 53m. There are 1704 mi between Cayman Islands and Boston. This flight may include one or multiple stops.

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

    On average you can expect to pay $992 for a flight from Cayman Islands to Boston. The cheapest flight overall is $217 while the most popular route, (George Town Owen Roberts Intl - Boston Logan Intl) is currently priced at $275.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Boston (average of $206). Flying from Cayman Islands to Boston in May is currently the most expensive (average of $460). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 2 airlines flying from Cayman Islands to Boston

Discover the top 2 airlines that operate flights from Cayman Islands to Boston. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$204Average$353FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$288Average$535FlexibilityNo cancel feeOn-time71%

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