$89+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Apr 12 — Apr 191
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 March 13, 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 March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/13. 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 4/46:00 am
BOS
- GCM
2 stops10h 05m
United Airlines
Wed 4/81:35 pm
GCM
- BOS
1 stop9h 05m
United Airlines
Deal found 3/13![United Airlines logo]()
$319
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:45 am
BOS
- GCM
1 stop8h 12m
Spirit Airlines
Thu 4/91:52 pm
GCM
- BOS
1 stop9h 07m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$323
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:45 am
BOS
- GCM
1 stop7h 35m
Spirit Airlines
Sat 4/41:15 pm
GCM
- BOS
1 stop9h 44m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:53 pm
BOS
- GCM
1 stop17h 02m
American Airlines
Mon 3/1612:00 pm
GCM
- BOS
1 stop8h 49m
American Airlines
Deal found 3/9![American Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 3/10. 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 3/177:34 pm
BOS
- GCM
2 stops18h 11m
United Airlines
Tue 3/241:25 pm
GCM
- BOS
1 stop7h 16m
United Airlines
Deal found 3/10![United Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/13. 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 4/246:00 am
BOS
- GCM
1 stop7h 00m
United Airlines
Wed 4/291:35 pm
GCM
- BOS
2 stops18h 50m
United Airlines
Deal found 3/13![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:35 am
BOS
- GCM
1 stop7h 25m
Delta
Mon 4/201:25 pm
GCM
- BOS
1 stop9h 33m
Delta
Deal found 3/10![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2212:45 pm
BOS
- GCM
1 stop7h 30m
American Airlines
Wed 3/257:45 am
GCM
- BOS
2 stops10h 41m
American Airlines
Deal found 3/9![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:25 am
BOS
- GCM
2 stops10h 50m
American Airlines
Tue 3/2412:00 pm
GCM
- BOS
2 stops10h 23m
American Airlines
Deal found 3/10![American Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 3/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:35 am
BOS
- GCM
1 stop7h 12m
Delta
Tue 3/171:12 pm
GCM
- BOS
1 stop11h 01m
Delta
Deal found 3/9![Delta logo]()
$338
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:15 am
BOS
- CYB
2 stops36h 35m
Multiple Airlines
Thu 4/26:20 pm
CYB
- BOS
2 stops27h 19m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$1,075
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 March 13, 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 March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/11. 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 5/265:47 am
BOS
- GCM
1 stop7h 43m
United Airlines
Sat 5/304:10 pm
GCM
- BOS
1 stop6h 49m
United Airlines
Deal found 3/11![United Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/9. 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 4/277:30 pm
BOS
- GCM
2 stops17h 15m
United Airlines
Sat 5/24:10 pm
GCM
- BOS
2 stops17h 10m
United Airlines
Deal found 3/9![United Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Sat 5/163:32 pm
BOS
- GCM
2 stops21h 58m
United Airlines
Sat 5/234:10 pm
GCM
- BOS
2 stops18h 06m
United Airlines
Deal found 3/9![United Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 3/9. 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 4/276:00 am
BOS
- GCM
1 stop6h 45m
United Airlines
Fri 5/11:35 pm
GCM
- BOS
2 stops20h 26m
United Airlines
Deal found 3/9![United Airlines logo]()
$398
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:15 am
BOS
- CYB
2 stops36h 35m
Multiple Airlines
Thu 4/26:20 pm
CYB
- BOS
2 stops27h 19m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$1,075
This United Airlines deal was found by Cheapflights users on 3/10. 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 4/16:00 am
BOS
- GCM
1 stop7h 45m
United Airlines
Thu 4/91:50 pm
GCM
- BOS
1 stop10h 09m
United Airlines
Deal found 3/10![United Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 3/12. 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 4/168:15 am
BOS
- GCM
2 stops29h 15m
United Airlines
Tue 4/211:35 pm
GCM
- BOS
1 stop9h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Fri 4/246:00 am
BOS
- GCM
1 stop7h 00m
United Airlines
Fri 5/11:35 pm
GCM
- BOS
2 stops20h 26m
United Airlines
Deal found 3/9![United Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 3/10. 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 3/3110:17 am
BOS
- GCM
1 stop27h 28m
United Airlines
Wed 4/81:35 pm
GCM
- BOS
1 stop9h 05m
United Airlines
Deal found 3/10![United Airlines logo]()
$421
Last-minute flights from Boston to Cayman IslandsDiscover last-minute flight deals from Boston to Cayman Islands. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Cayman Islands. Data last updated March 13, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:53 pm
BOS
- GCM
1 stop17h 02m
American Airlines
Mon 3/1612:00 pm
GCM
- BOS
1 stop8h 49m
American Airlines
Deal found 3/9![American Airlines logo]()
$325
This United Airlines deal was found by Cheapflights users on 3/10. 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 3/177:34 pm
BOS
- GCM
2 stops18h 11m
United Airlines
Tue 3/241:25 pm
GCM
- BOS
1 stop7h 16m
United Airlines
Deal found 3/10![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:25 am
BOS
- GCM
2 stops10h 50m
American Airlines
Tue 3/2412:00 pm
GCM
- BOS
2 stops10h 23m
American Airlines
Deal found 3/10![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2212:45 pm
BOS
- GCM
1 stop7h 30m
American Airlines
Wed 3/257:45 am
GCM
- BOS
2 stops10h 41m
American Airlines
Deal found 3/9![American Airlines logo]()
$331
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:45 am
BOS
- GCM
1 stop7h 35m
Spirit Airlines
Sat 4/41:15 pm
GCM
- BOS
1 stop9h 44m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$324
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:45 am
BOS
- GCM
1 stop7h 35m
Spirit Airlines
Thu 4/91:52 pm
GCM
- BOS
1 stop9h 07m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$338
This FlightHub deal was found by Cheapflights users on 3/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:15 am
BOS
- CYB
2 stops36h 35m
Multiple Airlines
Thu 4/26:20 pm
CYB
- BOS
2 stops27h 19m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$1,075
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/295:45 am
BOS
- GCM
1 stop8h 12m
Spirit Airlines
Thu 4/91:52 pm
GCM
- BOS
1 stop9h 07m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 3/13. 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 4/46:00 am
BOS
- GCM
2 stops10h 05m
United Airlines
Wed 4/81:35 pm
GCM
- BOS
1 stop9h 05m
United Airlines
Deal found 3/13![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:35 am
BOS
- GCM
1 stop7h 25m
Delta
Mon 4/201:25 pm
GCM
- BOS
1 stop9h 33m
Delta
Deal found 3/10![Delta logo]()
$329
This United Airlines deal was found by Cheapflights users on 3/13. 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 4/246:00 am
BOS
- GCM
1 stop7h 00m
United Airlines
Wed 4/291:35 pm
GCM
- BOS
2 stops18h 50m
United Airlines
Deal found 3/13![United Airlines logo]()
$328
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 March 13, 2026.
Search for one-way flight options from Boston to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Wed 4/86:00 am
BOS
- GCM
1 stop6h 45m
United Airlines
Deal found 3/9![United Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:53 pm
BOS
- GCM
2 stops17h 07m
American Airlines
Deal found 3/9![American Airlines logo]()
$95
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:45 am
BOS
- GCM
1 stop8h 40m
American Airlines
Deal found 3/9![American Airlines logo]()
$98
This American Airlines deal was found by Cheapflights users on 3/11. 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.
Wed 6/106:00 am
BOS
- GCM
2 stops11h 11m
American Airlines
Deal found 3/11![American Airlines logo]()
$104
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Mon 4/138:30 pm
BOS
- GCM
2 stops16h 01m
American Airlines
Deal found 3/13![American Airlines logo]()
$105
This Delta deal was found by Cheapflights users on 3/12. 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.
Fri 4/105:50 am
BOS
- GCM
1 stop8h 40m
Delta
Deal found 3/12![Delta logo]()
$109
This American Airlines deal was found by Cheapflights users on 3/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:36 pm
BOS
- GCM
2 stops16h 34m
American Airlines
Deal found 3/9![American Airlines logo]()
$110
This United Airlines deal was found by Cheapflights users on 3/10. 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 5/131:30 pm
BOS
- GCM
1 stop24h 00m
United Airlines
Deal found 3/10![United Airlines logo]()
$113
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/198:45 pm
BOS
- GCM
1 stop16h 02m
Delta
Deal found 3/10![Delta logo]()
$115
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
BOS
- GCM
2 stops8h 13m
American Airlines
Deal found 3/10![American Airlines logo]()
$116
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 March 13, 2026.
Round-trip from | $319 (United Airlines) |
|---|---|
One-way from | $89 (United Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $428 |
Good round-trip deal | $561 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 2,558,603 searches. Data last updated March 13, 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
Quickest round-trip
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Tue 5/26
5:47 am-12:30 pm
1 stop7h 43m
George Town Owen Roberts Intl
Sat 5/30
4:10 pm-11:59 pm
1 stop6h 49m
$331
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Mon 4/27
7:30 pm-11:45 am
2 stops17h 15m
George Town Owen Roberts Intl
Sat 5/2
4:10 pm-10:20 am
2 stops17h 10m
$398
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 5/16
3:32 pm-12:30 pm
2 stops21h 58m
George Town Owen Roberts Intl
Sat 5/23
4:10 pm-11:16 am
2 stops18h 06m
$398
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Mon 4/27
6:00 am-11:45 am
1 stop6h 45m
George Town Owen Roberts Intl
Fri 5/1
1:35 pm-11:01 am
2 stops20h 26m
$398
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Wed 4/1
6:00 am-12:45 pm
1 stop7h 45m
George Town Owen Roberts Intl
Thu 4/9
1:50 pm-12:59 am
1 stop10h 09m
$413
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Thu 4/16
8:15 am-12:30 pm
2 stops29h 15m
George Town Owen Roberts Intl
Tue 4/21
1:35 pm-11:40 pm
1 stop9h 05m
$418
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 4/24
6:00 am-12:00 pm
1 stop7h 00m
George Town Owen Roberts Intl
Fri 5/1
1:35 pm-11:01 am
2 stops20h 26m
$418
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Tue 3/31
10:17 am-12:45 pm
1 stop27h 28m
George Town Owen Roberts Intl
Wed 4/8
1:35 pm-11:40 pm
1 stop9h 05m
$421
BostonCayman Brac
BOS - CYB
BOSCYB
Boston Logan Intl
Sat 3/28
6:15 am-5:50 pm
2 stops36h 35m
Cayman Brac Gerrard-Smith
Thu 4/2
6:20 pm-10:39 pm
2 stops27h 19m
$1,075
Cheapest one-way
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Thu 4/23
6:00 am-12:45 pm
1 stop7h 45m
$89
Showing 1-10 of 19 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 $72). Flying from Boston to Cayman Islands in August is currently the most expensive (average of $404). 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 March 13, 2026.
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 March 13, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue 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
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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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Alternative routes for Boston to Cayman Islands
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Complete your trip
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Boston and Cayman Islands flights
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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 2,558,603 searches. Data last updated March 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$459 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$398 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$315 | Average$529 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$353 | Average$526 | FlexibilityNo cancel fee | On-time71% |