$134+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Cayman Islands with Cheapflights
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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
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Cheapest flights from Boston to Cayman IslandsExplore 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 August 21, 2026.
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 August 21, 2026.
This CheapTickets.ch deal was found by Cheapflights users on 8/18. 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 CheapTickets.ch is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2511:10 am -
1 stop25h 00m
Sun 11/291:10 pm -
1 stop19h 34m
Deal found 8/18![Air Canada logo]()
$357
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:10 am -
1 stop25h 00m
Fri 11/131:10 pm -
1 stop9h 27m
Deal found 8/17![Air Canada logo]()
$363
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:00 pm -
1 stop19h 30m
Sat 10/2412:25 pm -
1 stop20h 52m
Deal found 8/17![Air Canada logo]()
$367
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:50 pm -
2 stops41h 40m
Thu 10/2212:25 pm -
1 stop20h 30m
Deal found 8/17![Air Canada logo]()
$370
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:50 am -
2 stops30h 40m
Thu 10/2212:25 pm -
2 stops25h 16m
Deal found 8/17![Air Canada logo]()
$373
This Trip.com deal was found by Cheapflights users on 8/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/263:10 pm -
1 stop21h 00m
Sun 11/291:10 pm -
1 stop19h 34m
Deal found 8/21![Air Canada logo]()
$376
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sun 10/116:00 am -
1 stop6h 00m
Mon 10/198:00 am -
1 stop7h 06m
Deal found 8/21![American Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/17. 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 12/56:00 am -
2 stops10h 35m
Sat 12/125:30 pm -
1 stop6h 24m
Deal found 8/17![United Airlines logo]()
$393
This FlightHub deal was found by Cheapflights users on 8/19. 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.
Fri 12/253:10 pm -
2 stops24h 00m
Wed 12/303:55 pm -
2 stops30h 42m
Deal found 8/19![Multiple Airlines logo]()
$1,924
Best flights from Boston to Cayman IslandsDiscover carefully curated flight deals from Boston to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Boston to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/20. 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 11/45:30 am -
2 stops11h 00m
Sun 11/85:45 pm -
1 stop18h 40m
Deal found 8/20![United Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/17. 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.
Sat 9/125:30 am -
1 stop7h 10m
Mon 9/141:00 pm -
1 stop8h 33m
Deal found 8/17![Delta logo]()
$393
This JetBlue deal was found by Cheapflights users on 8/19. 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 1/307:08 am -
1 stop7h 24m
Sat 2/132:30 pm -
Nonstop4h 10m
Deal found 8/19![JetBlue logo]()
$678
This United Airlines deal was found by Cheapflights users on 8/21. 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 12/55:00 pm -
3 stops23h 30m
Sat 12/125:10 pm -
2 stops19h 13m
Deal found 8/21![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/18. 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 12/128:25 pm -
2 stops20h 05m
Sat 12/195:30 pm -
2 stops16h 47m
Deal found 8/18![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/17. 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 1/237:35 pm -
2 stops17h 40m
Sat 1/305:30 pm -
2 stops16h 25m
Deal found 8/17![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/168:25 pm -
2 stops17h 00m
Tue 10/274:45 pm -
1 stop18h 40m
Deal found 8/21![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/17. 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 11/118:25 pm -
2 stops20h 05m
Mon 11/165:45 pm -
2 stops27h 45m
Deal found 8/17![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/20. 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 1/47:49 pm -
2 stops41h 26m
Thu 1/142:50 pm -
2 stops24h 35m
Deal found 8/20![United Airlines logo]()
$532
This Justfly.com deal was found by Cheapflights users on 8/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:40 pm -
2 stops19h 30m
Thu 12/318:30 am -
2 stops14h 07m
Deal found 8/19![Multiple Airlines logo]()
$1,924
This United Airlines deal was found by Cheapflights users on 8/17. 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 11/115:30 am -
2 stops11h 00m
Sun 11/155:45 pm -
2 stops15h 38m
Deal found 8/17![United Airlines logo]()
$553
This United Airlines deal was found by Cheapflights users on 8/19. 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 12/249:30 am -
2 stops30h 30m
Thu 12/315:45 pm -
2 stops30h 14m
Deal found 8/19![United Airlines logo]()
$664
This United Airlines deal was found by Cheapflights users on 8/19. 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 11/265:30 am -
2 stops11h 00m
Mon 11/305:45 pm -
2 stops15h 39m
Deal found 8/19![United Airlines logo]()
$687
This FlightHub deal was found by Cheapflights users on 8/19. 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.
Fri 12/253:10 pm -
2 stops24h 00m
Wed 12/303:55 pm -
2 stops30h 42m
Deal found 8/19![Multiple Airlines logo]()
$1,924
Last-minute flights from Boston to Cayman IslandsDiscover last-minute flight deals from Boston to Cayman Islands. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Cayman Islands. Data last updated August 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/55:51 am -
1 stop9h 26m
Fri 9/1112:36 pm -
1 stop8h 48m
Deal found 8/19![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/106:05 am -
1 stop6h 22m
Mon 9/1412:36 pm -
1 stop8h 48m
Deal found 8/18![American Airlines logo]()
$393
This FlightHub deal was found by Cheapflights users on 8/17. 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.
Thu 9/106:50 pm -
2 stops39h 55m
Mon 9/1412:25 pm -
1 stop9h 15m
Deal found 8/17![Air Canada logo]()
$402
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/108:45 pm -
2 stops15h 42m
Sun 9/1312:36 pm -
2 stops11h 23m
Deal found 8/18![American Airlines logo]()
$403
This Air Canada deal was found by Cheapflights users on 8/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:50 pm -
2 stops39h 55m
Thu 9/1712:25 pm -
1 stop28h 39m
Deal found 8/19![Air Canada logo]()
$422
This Delta deal was found by Cheapflights users on 8/19. 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 9/108:57 pm -
1 stop15h 43m
Thu 9/171:00 pm -
1 stop11h 17m
Deal found 8/19![Delta logo]()
$424
This Expedia deal was found by Cheapflights users on 8/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2512:30 pm -
1 stop22h 15m
Mon 9/2812:25 pm -
1 stop9h 15m
Deal found 8/18![Air Canada logo]()
$407
One-way flights from Boston to Cayman IslandsSearch for one-way flight options from Boston to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Boston to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Orbitz deal was found by Cheapflights users on 8/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:00 pm -
1 stop19h 25m
Deal found 8/19![Air Canada logo]()
$134
This Air Canada deal was found by Cheapflights users on 8/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:30 pm -
1 stop23h 00m
Deal found 8/18![Air Canada logo]()
$139
This Orbitz deal was found by Cheapflights users on 8/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop28h 45m
Deal found 8/18![Air Canada logo]()
$143
This Delta deal was found by Cheapflights users on 8/17. 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 11/175:30 am -
1 stop6h 55m
Deal found 8/17![Delta logo]()
$144
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:50 pm -
2 stops41h 40m
Deal found 8/17![Air Canada logo]()
$148
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/188:31 pm -
2 stops16h 54m
Deal found 8/18![United Airlines logo]()
$150
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:35 pm -
2 stops17h 35m
Deal found 8/17![Air Canada logo]()
$151
This Air Canada deal was found by Cheapflights users on 8/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:50 pm -
2 stops17h 35m
Deal found 8/17![Air Canada logo]()
$153
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 August 21, 2026.
Round-trip from | $357 (CheapTickets.ch) |
|---|---|
One-way from | $134 (Orbitz) |
Popular in | December |
Cheapest in | January |
Average price | $566 |
Good round-trip deal | $816 or less |
Good one-way deal | $298 or less |
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 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Boston to the Cayman Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Wed 11/4
5:30 am-4:30 pm
2 stops11h 00m
George Town Owen Roberts Intl
Sun 11/8
5:45 pm-12:25 pm
1 stop18h 40m
$393
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 9/12
5:30 am-11:40 am
1 stop7h 10m
George Town Owen Roberts Intl
Mon 9/14
1:00 pm-10:33 pm
1 stop8h 33m
$393
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 12/5
5:00 pm-4:30 pm
3 stops23h 30m
George Town Owen Roberts Intl
Sat 12/12
5:10 pm-12:23 pm
2 stops19h 13m
$518
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 12/12
8:25 pm-4:30 pm
2 stops20h 05m
George Town Owen Roberts Intl
Sat 12/19
5:30 pm-10:17 am
2 stops16h 47m
$518
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 1/23
7:35 pm-1:15 pm
2 stops17h 40m
George Town Owen Roberts Intl
Sat 1/30
5:30 pm-9:55 am
2 stops16h 25m
$518
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Fri 10/16
8:25 pm-12:25 pm
2 stops17h 00m
George Town Owen Roberts Intl
Tue 10/27
4:45 pm-12:25 pm
1 stop18h 40m
$518
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Wed 11/11
8:25 pm-4:30 pm
2 stops20h 05m
George Town Owen Roberts Intl
Mon 11/16
5:45 pm-9:30 pm
2 stops27h 45m
$518
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Mon 1/4
7:49 pm-1:15 pm
2 stops41h 26m
George Town Owen Roberts Intl
Thu 1/14
2:50 pm-3:25 pm
2 stops24h 35m
$532
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Wed 11/11
5:30 am-4:30 pm
2 stops11h 00m
George Town Owen Roberts Intl
Sun 11/15
5:45 pm-9:23 am
2 stops15h 38m
$553
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Thu 12/24
9:30 am-4:00 pm
2 stops30h 30m
George Town Owen Roberts Intl
Thu 12/31
5:45 pm-11:59 pm
2 stops30h 14m
$664
Showing 1-10 of 24 resultsSorted by cheapest first
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.
BOS-GCM
BOS-CYB
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
BOS-KY0
BOS-GCM
BOS-CYB
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 $363). Flying from Boston to Cayman Islands in December is currently the most expensive (average of $690). 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.
How far ahead should I book a flight from Boston to Cayman Islands?
Booking 47 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Cayman Islands. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 August 21, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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.
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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.
Complete your trip
Complete your trip to Cayman Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Cayman Islands by cabin class
Find flights from Boston to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Cayman Islands flights
Browse other Boston and Cayman Islands flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Cayman Islands regions
Consider these flights traveling to Cayman Islands regions.
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 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$391 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$553 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$330 | Average$559 | FlexibilityNo cancel fee | On-time71% |