$91+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Jun 14 — Jun 211
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Cayman Islands with Cheapflights
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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 May 15, 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 May 15, 2026.
This Delta deal was found by Cheapflights users on 5/12. 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.
Thu 6/45:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/1012:59 pm
GCM
- BOS
1 stop11h 32m
Delta
Deal found 5/12![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 5/201:19 pm
GCM
- BOS
1 stop11h 04m
Delta
Deal found 5/11![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:35 am
BOS
- GCM
1 stop7h 19m
Delta
Sat 5/301:19 pm
GCM
- BOS
1 stop11h 09m
Delta
Deal found 5/11![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Thu 6/45:31 am
BOS
- GCM
2 stops11h 40m
American Airlines
Wed 6/105:12 pm
GCM
- BOS
2 stops13h 27m
American Airlines
Deal found 5/11![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 5/11. 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 7/157:04 am
BOS
- GCM
2 stops10h 06m
American Airlines
Wed 7/2912:02 pm
GCM
- BOS
2 stops9h 31m
American Airlines
Deal found 5/11![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 6/65:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/1012:59 pm
GCM
- BOS
1 stop11h 32m
Delta
Deal found 5/12![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 5/10. 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.
Sat 8/157:20 pm
BOS
- GCM
1 stop17h 19m
Delta
Sat 8/221:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 5/10![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 5/14. 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 11/76:00 am
BOS
- GCM
1 stop10h 35m
United Airlines
Sat 11/212:50 pm
GCM
- BOS
1 stop10h 12m
United Airlines
Deal found 5/14![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/11. 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.
Sat 6/65:47 am
BOS
- GCM
1 stop7h 43m
United Airlines
Wed 6/101:35 pm
GCM
- BOS
2 stops17h 42m
United Airlines
Deal found 5/11![United Airlines logo]()
$353
This FlightHub deal was found by Cheapflights users on 5/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- GCM
1 stop7h 45m
JetBlue
Thu 6/42:05 pm
GCM
- BOS
2 stops16h 12m
JetBlue
Deal found 5/11![JetBlue logo]()
$368
This Cheapflightsfares deal was found by Cheapflights users on 5/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
BOS
- GCM
1 stop8h 00m
JetBlue
Tue 6/92:05 pm
GCM
- BOS
1 stop8h 22m
JetBlue
Deal found 5/10![JetBlue logo]()
$370
This Kissandfly.com deal was found by Cheapflights users on 5/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/152:12 pm
BOS
- GCM
1 stop22h 19m
British Airways
Sat 5/2312:31 pm
GCM
- BOS
1 stop7h 29m
British Airways
Deal found 5/11![British Airways logo]()
$372
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 May 15, 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 May 15, 2026.
This Delta deal was found by Cheapflights users on 5/14. 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 6/65:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/1012:59 pm
GCM
- BOS
1 stop11h 32m
Delta
Deal found 5/14![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 5/14. 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 11/76:00 am
BOS
- GCM
1 stop10h 35m
United Airlines
Sat 11/212:50 pm
GCM
- BOS
1 stop10h 12m
United Airlines
Deal found 5/14![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/11. 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.
Sat 6/65:45 am
BOS
- GCM
1 stop10h 25m
United Airlines
Wed 6/101:35 pm
GCM
- BOS
1 stop8h 44m
United Airlines
Deal found 5/11![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 5/10. 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.
Sat 6/66:00 am
BOS
- GCM
1 stop8h 30m
United Airlines
Tue 6/91:35 pm
GCM
- BOS
2 stops17h 42m
United Airlines
Deal found 5/10![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 5/305:35 am
BOS
- GCM
1 stop7h 19m
Delta
Thu 6/41:19 pm
GCM
- BOS
1 stop9h 38m
Delta
Deal found 5/12![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 5/12. 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.
Tue 5/265:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/31:19 pm
GCM
- BOS
1 stop11h 09m
Delta
Deal found 5/12![Delta logo]()
$412
This United Airlines deal was found by Cheapflights users on 5/14. 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 11/76:00 am
BOS
- GCM
1 stop7h 45m
United Airlines
Sat 11/145:45 pm
GCM
- BOS
2 stops15h 39m
United Airlines
Deal found 5/14![United Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 5/14. 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 8/297:30 am
BOS
- GCM
1 stop7h 05m
United Airlines
Sat 9/51:35 pm
GCM
- BOS
2 stops19h 01m
United Airlines
Deal found 5/14![United Airlines logo]()
$408
This FlightHub deal was found by Cheapflights users on 5/14. 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.
Wed 7/154:55 pm
BOS
- CYB
2 stops23h 30m
Multiple Airlines
Tue 7/216:20 pm
CYB
- BOS
2 stops29h 39m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$1,207
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 7/38:15 pm
BOS
- GCM
2 stops20h 20m
United Airlines
Thu 7/91:35 pm
GCM
- BOS
2 stops31h 21m
United Airlines
Deal found 5/12![United Airlines logo]()
$423
Last-minute flights from Boston to Cayman IslandsDiscover last-minute flight deals from Boston to Cayman Islands. Data last updated May 15, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Cayman Islands. Data last updated May 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/135:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 5/201:19 pm
GCM
- BOS
1 stop11h 04m
Delta
Deal found 5/11![Delta logo]()
$314
This Kissandfly.com deal was found by Cheapflights users on 5/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/152:12 pm
BOS
- GCM
1 stop22h 19m
British Airways
Sat 5/2312:31 pm
GCM
- BOS
1 stop7h 29m
British Airways
Deal found 5/11![British Airways logo]()
$372
This Delta deal was found by Cheapflights users on 5/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:35 am
BOS
- GCM
1 stop7h 19m
Delta
Sat 5/301:19 pm
GCM
- BOS
1 stop11h 09m
Delta
Deal found 5/11![Delta logo]()
$321
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:59 am
BOS
- GCM
1 stop6h 01m
JetBlue
Thu 6/42:05 pm
GCM
- BOS
2 stops16h 12m
JetBlue
Deal found 5/10![JetBlue logo]()
$379
This American Airlines deal was found by Cheapflights users on 5/11. 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 5/306:00 am
BOS
- GCM
2 stops10h 07m
American Airlines
Sat 6/611:55 am
GCM
- BOS
2 stops9h 27m
American Airlines
Deal found 5/11![American Airlines logo]()
$397
This FlightHub deal was found by Cheapflights users on 5/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- GCM
1 stop7h 45m
JetBlue
Thu 6/42:05 pm
GCM
- BOS
2 stops16h 12m
JetBlue
Deal found 5/11![JetBlue logo]()
$368
This Delta deal was found by Cheapflights users on 5/12. 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.
Thu 6/45:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/1012:59 pm
GCM
- BOS
1 stop11h 32m
Delta
Deal found 5/12![Delta logo]()
$313
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Thu 6/45:01 am
BOS
- GCM
1 stop12h 10m
American Airlines
Wed 6/105:12 pm
GCM
- BOS
2 stops13h 27m
American Airlines
Deal found 5/11![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 6/65:35 am
BOS
- GCM
1 stop7h 19m
Delta
Wed 6/1012:59 pm
GCM
- BOS
1 stop11h 32m
Delta
Deal found 5/12![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 5/11. 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.
Sat 6/65:45 am
BOS
- GCM
1 stop10h 25m
United Airlines
Wed 6/101:35 pm
GCM
- BOS
1 stop8h 44m
United Airlines
Deal found 5/11![United Airlines logo]()
$348
This Cheapflightsfares deal was found by Cheapflights users on 5/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
BOS
- GCM
1 stop8h 00m
JetBlue
Tue 6/92:05 pm
GCM
- BOS
1 stop8h 22m
JetBlue
Deal found 5/10![JetBlue logo]()
$370
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 May 15, 2026.
Search for one-way flight options from Boston to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated May 15, 2026.
This JetBlue deal was found by Cheapflights users on 5/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- GCM
1 stop7h 45m
JetBlue
Deal found 5/10![JetBlue logo]()
$91
This Delta deal was found by Cheapflights users on 5/12. 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.
Thu 6/45:35 am
BOS
- GCM
1 stop7h 19m
Delta
Deal found 5/12![Delta logo]()
$104
This United Airlines deal was found by Cheapflights users on 5/10. 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 6/58:26 pm
BOS
- GCM
2 stops17h 04m
United Airlines
Deal found 5/10![United Airlines logo]()
$110
This Delta deal was found by Cheapflights users on 5/10. 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.
Sat 7/47:25 pm
BOS
- GCM
1 stop17h 09m
Delta
Deal found 5/10![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 5/12. 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.
Sat 6/65:35 am
BOS
- GCM
1 stop7h 19m
Delta
Deal found 5/12![Delta logo]()
$126
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Sun 11/86:00 am
BOS
- GCM
2 stops10h 30m
United Airlines
Deal found 5/13![United Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Fri 7/34:06 pm
BOS
- GCM
1 stop19h 17m
American Airlines
Deal found 5/11![American Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Tue 7/288:15 pm
BOS
- GCM
2 stops17h 15m
United Airlines
Deal found 5/12![United Airlines logo]()
$145
This American Airlines deal was found by Cheapflights users on 5/11. 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 7/86:00 am
BOS
- GCM
2 stops11h 10m
American Airlines
Deal found 5/11![American Airlines logo]()
$148
This United Airlines deal was found by Cheapflights users on 5/10. 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 11/37:40 am
BOS
- GCM
1 stop8h 50m
United Airlines
Deal found 5/10![United Airlines logo]()
$149
This Expedia deal was found by Cheapflights users on 5/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:55 pm
BOS
- GCM
1 stop17h 30m
Air Canada
Deal found 5/12![Air Canada logo]()
$152
This United Airlines deal was found by Cheapflights users on 5/13. 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 11/78:10 pm
BOS
- GCM
2 stops20h 20m
United Airlines
Deal found 5/13![United Airlines logo]()
$155
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 May 15, 2026.
Round-trip from | $313 (Delta) |
|---|---|
One-way from | $91 (JetBlue) |
Popular in | December |
Cheapest in | January |
Average price | $480 |
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 May 15, 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 - GCM
BOSGCM
Boston Logan Intl
Sat 6/6
5:35 am-11:54 am
1 stop7h 19m
George Town Owen Roberts Intl
Wed 6/10
12:59 pm-1:31 am
1 stop11h 32m
$335
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 11/7
6:00 am-4:35 pm
1 stop10h 35m
George Town Owen Roberts Intl
Sat 11/21
2:50 pm-1:02 am
1 stop10h 12m
$348
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 6/6
5:45 am-3:10 pm
1 stop10h 25m
George Town Owen Roberts Intl
Wed 6/10
1:35 pm-11:19 pm
1 stop8h 44m
$348
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 6/6
6:00 am-1:30 pm
1 stop8h 30m
George Town Owen Roberts Intl
Tue 6/9
1:35 pm-8:17 am
2 stops17h 42m
$353
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 11/7
6:00 am-1:45 pm
1 stop7h 45m
George Town Owen Roberts Intl
Sat 11/14
5:45 pm-9:24 am
2 stops15h 39m
$387
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 8/29
7:30 am-1:35 pm
1 stop7h 05m
George Town Owen Roberts Intl
Sat 9/5
1:35 pm-9:36 am
2 stops19h 01m
$408
Quickest round-trip
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 5/30
5:35 am-11:54 am
1 stop7h 19m
George Town Owen Roberts Intl
Thu 6/4
1:19 pm-11:57 pm
1 stop9h 38m
$412
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Tue 5/26
5:35 am-11:54 am
1 stop7h 19m
George Town Owen Roberts Intl
Wed 6/3
1:19 pm-1:28 am
1 stop11h 09m
$412
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 7/3
8:15 pm-3:35 pm
2 stops20h 20m
George Town Owen Roberts Intl
Thu 7/9
1:35 pm-9:56 pm
2 stops31h 21m
$423
BostonCayman Brac
BOS - CYB
BOSCYB
Boston Logan Intl
Wed 7/15
4:55 pm-3:25 pm
2 stops23h 30m
Cayman Brac Gerrard-Smith
Tue 7/21
6:20 pm-12:59 am
2 stops29h 39m
$1,207
Showing 1-10 of 20 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
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.
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 October is currently the most expensive (average of $329). 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 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 May 15, 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.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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
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 May 15, 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 2,558,603 searches. Data last updated May 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$448 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$404 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$315 | Average$536 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$332 | Average$527 | FlexibilityNo cancel fee | On-time71% |