HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$88+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Cayman Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 octubre 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$271
(American Airlines)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$469

Good round-trip deal

$385 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
Search Deals
From Boston Logan Intl to Cayman Islands
Search Deals
One-way flight from Boston Logan Intl to Cayman Islands
Search Deals
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 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 Boston Logan Intl to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Cayman Islands.
Search Deals

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 octubre 29, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
sáb. 11/295:40 amBOS - GCM
1 stop5h 54mAmerican Airlines
sáb. 12/63:19 pmGCM - BOS
1 stop7h 25mAmerican Airlines
Deal found 10/28$271
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.
mié. 12/316:45 amBOS - GCM
1 stop6h 30mUnited Airlines
lun. 1/122:25 pmGCM - BOS
1 stop7h 27mUnited Airlines
Deal found 10/27$277
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/66:36 pmBOS - GCM
1 stop17h 24mAmerican Airlines
mar. 12/98:45 amGCM - BOS
1 stop12h 11mAmerican Airlines
Deal found 10/29$280
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.
mar. 10/287:00 amBOS - GCM
1 stop9h 30mUnited Airlines
mar. 11/45:45 pmGCM - BOS
1 stop18h 41mUnited Airlines
Deal found 10/27$284
This United Airlines deal was found by Cheapflights users on 10/28. 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.
vie. 10/317:00 amBOS - GCM
1 stop9h 30mUnited Airlines
lun. 11/35:45 pmGCM - BOS
2 stops21h 37mUnited Airlines
Deal found 10/28$289
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.
lun. 12/154:40 pmBOS - GCM
1 stop23h 50mUnited Airlines
vie. 12/192:25 pmGCM - BOS
1 stop8h 23mUnited Airlines
Deal found 10/27$292
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.
mié. 11/198:33 amBOS - GCM
2 stops11h 55mAmerican Airlines
dom. 11/233:10 pmGCM - BOS
1 stop19h 19mAmerican Airlines
Deal found 10/27$296
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.
jue. 12/255:20 amBOS - GCM
1 stop11h 15mUnited Airlines
mar. 12/305:10 pmGCM - BOS
1 stop6h 44mUnited Airlines
Deal found 10/27$299
This United Airlines deal was found by Cheapflights users on 10/28. 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.
vie. 12/57:00 amBOS - GCM
1 stop9h 30mUnited Airlines
lun. 12/85:45 pmGCM - BOS
1 stop18h 36mUnited Airlines
Deal found 10/28$306
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/712:14 pmBOS - CYB
2 stops25h 06mMultiple Airlines
dom. 11/910:55 amCYB - BOS
2 stops11h 42mMultiple Airlines
Deal found 10/28$948

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 octubre 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

mié. 2/4

7:07 pm-1:15 pm

2 stops18h 08m

George Town Owen Roberts Intl

lun. 2/9

2:25 pm-9:52 pm

1 stop7h 27m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mié. 2/25

6:00 am-1:15 pm

1 stop7h 15m

George Town Owen Roberts Intl

mié. 3/4

2:25 pm-9:51 pm

1 stop7h 26m

$284

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

vie. 1/2

9:30 am-4:35 pm

1 stop7h 05m

George Town Owen Roberts Intl

jue. 1/8

2:25 pm-11:49 pm

2 stops9h 24m

$289

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

sáb. 1/3

6:45 am-1:15 pm

1 stop6h 30m

George Town Owen Roberts Intl

sáb. 1/10

5:45 pm-10:52 am

2 stops17h 07m

$289

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

lun. 1/12

6:23 pm-11:26 am

1 stop17h 03m

George Town Owen Roberts Intl

sáb. 1/17

12:16 pm-8:33 pm

1 stop8h 17m

$305

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

dom. 1/25

6:45 pm-12:40 pm

1 stop17h 55m

George Town Owen Roberts Intl

sáb. 1/31

2:15 pm-7:33 am

1 stop17h 18m

$310

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

lun. 1/26

5:35 am-12:40 pm

1 stop7h 05m

George Town Owen Roberts Intl

sáb. 1/31

2:15 pm-7:33 am

1 stop17h 18m

$310

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mar. 3/24

5:40 am-11:35 am

1 stop6h 55m

George Town Owen Roberts Intl

sáb. 3/28

1:15 pm-10:33 pm

1 stop8h 18m

$310

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

mié. 2/4

5:35 am-12:40 pm

1 stop7h 05m

George Town Owen Roberts Intl

mié. 2/11

2:05 pm-1:04 am

1 stop10h 59m

$320

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

lun. 2/2

8:20 pm-12:40 pm

1 stop16h 20m

George Town Owen Roberts Intl

mar. 2/10

2:05 pm-10:32 pm

1 stop8h 27m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 24 results
1
2
3

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, November is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $235). Flying from Boston to Cayman Islands in June is currently the most expensive (average of $419). 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 octubre 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Boston to Cayman Islands in the afternoon. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the morning.

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 octubre 29, 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
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
2,907 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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 and American Airlines can get you from Boston to Cayman Islands in just under 17h 03m. Your travel time can differ by up to 1h 05m. 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 flights from Boston to Cayman Islands?

    Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $284 on average, our data indicates $334 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, November is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $235). Flying from Boston to Cayman Islands in June is currently the most expensive (average of $419). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Boston to Oranjestad flights
Hartford to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
Boston to Saint Thomas Island flights
Boston to Santiago de los Caballeros flights
Boston to Montego Bay flights
Boston to Nassau flights
Boston to Simpson Bay flights
Boston to Providenciales flights
Boston to Bridgetown flights
Boston to George Town flights
Boston to Castries flights
Hartford to Oranjestad flights
Boston to Christiansted flights
Albany to Luis Munoz Marin Intl flights
Boston to Willemstad flights
Hartford to Punta Cana flights
Hartford to Montego Bay flights
Boston to Kingston flights
Boston to St. John's flights
Hartford to Saint Thomas Island flights
Boston to Basseterre flights
Boston to Road Town flights
Albany to Oranjestad flights
Boston to St. George's flights
Boston to Port of Spain flights
Boston to The Valley flights
Hartford to Castries flights
Hartford to Santo Domingo flights
Hartford to Christiansted flights
Hartford to Nassau flights
Albany to Punta Cana flights
Boston to Puerto Plata flights
Boston to Gregory Town flights
Worcester to Luis Munoz Marin Intl flights
Hartford to Kingston flights
Boston to Kralendijk flights
Hartford to Simpson Bay flights
Boston to Aguadilla flights
Albany to Saint Thomas Island flights
Boston to Kingstown flights
Albany to Nassau flights
Boston to Freeport flights
Boston to Ponce flights
Hartford to Aguadilla flights
Hartford to Providenciales flights
Albany to Montego Bay flights
Boston to Georgetown flights

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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$489FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$261Average$460FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$270Average$412FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$330Average$541FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$457Average$559FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$469Average$868FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.