$119+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Aug 6 — Aug 131
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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Best
Last-minute
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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 July 7, 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 July 7, 2026.
This Delta deal was found by Cheapflights users on 7/6. 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 9/105:30 am
BOS
- GCM
1 stop7h 10m
Delta
Thu 9/171:00 pm
GCM
- BOS
1 stop8h 31m
Delta
Deal found 7/6![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/218:31 pm
BOS
- GCM
2 stops16h 54m
United Airlines
Sat 8/291:35 pm
GCM
- BOS
1 stop9h 03m
United Airlines
Deal found 7/3![United Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 7/7. 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 10/248:31 pm
BOS
- GCM
2 stops19h 59m
United Airlines
Fri 10/304:45 pm
GCM
- BOS
2 stops15h 54m
United Airlines
Deal found 7/7![United Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 7/3. 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 7/45:30 am
BOS
- GCM
1 stop7h 04m
Delta
Wed 7/812:56 pm
GCM
- BOS
1 stop11h 24m
Delta
Deal found 7/3![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/49:25 am
BOS
- GCM
1 stop6h 45m
United Airlines
Wed 7/81:35 pm
GCM
- BOS
2 stops21h 17m
United Airlines
Deal found 7/3![United Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:31 pm
BOS
- GCM
2 stops40h 54m
United Airlines
Sun 10/41:35 pm
GCM
- BOS
1 stop9h 04m
United Airlines
Deal found 7/7![United Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 7/7. 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 7/85:47 am
BOS
- GCM
1 stop7h 43m
United Airlines
Wed 7/151:35 pm
GCM
- BOS
1 stop8h 44m
United Airlines
Deal found 7/7![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 7/6. 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 11/117:25 am
BOS
- GCM
1 stop9h 05m
United Airlines
Sun 11/155:45 pm
GCM
- BOS
2 stops15h 54m
United Airlines
Deal found 7/6![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:00 pm
BOS
- GCM
2 stops15h 35m
Southwest
Wed 11/111:30 pm
GCM
- BOS
2 stops18h 35m
Southwest
Deal found 7/6![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 7/7. 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 10/18:56 pm
BOS
- GCM
1 stop15h 44m
Delta
Sun 10/41:00 pm
GCM
- BOS
1 stop8h 31m
Delta
Deal found 7/7![Delta logo]()
$399
This FlightHub deal was found by Cheapflights users on 7/5. 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 12/257:40 pm
BOS
- CYB
2 stops22h 10m
Multiple Airlines
Wed 12/3010:55 am
CYB
- BOS
2 stops23h 17m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$1,600
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 July 7, 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 July 7, 2026.
This Delta deal was found by Cheapflights users on 7/6. 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 8/285:30 am
BOS
- GCM
1 stop7h 09m
Delta
Mon 8/311:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/6![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/4. 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 11/146:00 am
BOS
- GCM
2 stops10h 35m
United Airlines
Sat 11/212:50 pm
GCM
- BOS
1 stop8h 32m
United Airlines
Deal found 7/4![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:00 pm
BOS
- GCM
2 stops15h 35m
Southwest
Wed 11/111:30 pm
GCM
- BOS
2 stops18h 35m
Southwest
Deal found 7/6![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 7/4. 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 8/255:30 am
BOS
- GCM
1 stop7h 09m
Delta
Tue 9/11:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/4![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/218:31 pm
BOS
- GCM
2 stops16h 54m
United Airlines
Sat 8/291:35 pm
GCM
- BOS
2 stops19h 01m
United Airlines
Deal found 7/3![United Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 7/4. 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 8/295:30 am
BOS
- GCM
1 stop7h 09m
Delta
Mon 8/311:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/4![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:31 pm
BOS
- GCM
2 stops40h 54m
United Airlines
Sun 10/41:35 pm
GCM
- BOS
1 stop9h 04m
United Airlines
Deal found 7/7![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 7/6. 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 8/215:30 am
BOS
- GCM
1 stop7h 09m
Delta
Tue 8/251:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/6![Delta logo]()
$455
This United Airlines deal was found by Cheapflights users on 7/2. 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 7/298:15 pm
BOS
- GCM
2 stops17h 15m
United Airlines
Tue 8/41:35 pm
GCM
- BOS
1 stop8h 55m
United Airlines
Deal found 7/2![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/5. 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 1/36:00 am
BOS
- GCM
1 stop10h 35m
United Airlines
Thu 1/72:50 pm
GCM
- BOS
1 stop18h 34m
United Airlines
Deal found 7/5![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 7/4. 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
2 stops10h 20m
United Airlines
Mon 11/95:45 pm
GCM
- BOS
2 stops29h 55m
United Airlines
Deal found 7/4![United Airlines logo]()
$468
This FlightHub deal was found by Cheapflights users on 7/5. 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 12/257:40 pm
BOS
- CYB
2 stops22h 10m
Multiple Airlines
Wed 12/3010:55 am
CYB
- BOS
2 stops23h 17m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$1,600
Last-minute flights from Boston to Cayman IslandsDiscover last-minute flight deals from Boston to Cayman Islands. Data last updated July 7, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Cayman Islands. Data last updated July 7, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/7. 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 7/85:47 am
BOS
- GCM
1 stop7h 43m
United Airlines
Wed 7/151:35 pm
GCM
- BOS
1 stop8h 44m
United Airlines
Deal found 7/7![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 7/6. 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 7/165:30 am
BOS
- GCM
1 stop7h 01m
Delta
Wed 7/2212:56 pm
GCM
- BOS
1 stop11h 24m
Delta
Deal found 7/6![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 7/6. 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 7/165:30 am
BOS
- GCM
1 stop7h 01m
Delta
Mon 7/2012:56 pm
GCM
- BOS
1 stop11h 24m
Delta
Deal found 7/6![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/218:31 pm
BOS
- GCM
2 stops16h 54m
United Airlines
Sat 8/291:35 pm
GCM
- BOS
1 stop9h 03m
United Airlines
Deal found 7/3![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 7/6. 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 8/215:30 am
BOS
- GCM
1 stop7h 09m
Delta
Tue 8/251:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/6![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 7/7. 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 8/225:30 am
BOS
- GCM
1 stop7h 09m
Delta
Sat 8/291:04 pm
GCM
- BOS
1 stop7h 26m
Delta
Deal found 7/7![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 7/5. 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.
Mon 8/245:30 am
BOS
- GCM
1 stop7h 09m
Delta
Fri 8/281:04 pm
GCM
- BOS
1 stop9h 37m
Delta
Deal found 7/5![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 7/6. 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 8/295:30 am
BOS
- GCM
1 stop7h 09m
Delta
Mon 8/311:04 pm
GCM
- BOS
1 stop11h 21m
Delta
Deal found 7/6![Delta logo]()
$343
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 July 7, 2026.
Search for one-way flight options from Boston to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated July 7, 2026.
This Delta deal was found by Cheapflights users on 7/3. 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 12/318:00 am
BOS
- GCM
1 stop6h 30m
Delta
Deal found 7/3![Delta logo]()
$119
This United Airlines deal was found by Cheapflights users on 7/4. 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 10/26:43 pm
BOS
- GCM
2 stops18h 42m
United Airlines
Deal found 7/4![United Airlines logo]()
$123
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:05 pm
BOS
- GCM
2 stops17h 40m
United Airlines
Deal found 7/3![United Airlines logo]()
$125
This United Airlines deal was found by Cheapflights users on 7/5. 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 11/128:25 pm
BOS
- GCM
2 stops20h 05m
United Airlines
Deal found 7/5![United Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 7/6. 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 9/46:00 pm
BOS
- GCM
1 stop20h 35m
United Airlines
Deal found 7/6![United Airlines logo]()
$131
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:31 pm
BOS
- GCM
2 stops40h 54m
United Airlines
Deal found 7/3![United Airlines logo]()
$144
This United Airlines deal was found by Cheapflights users on 7/5. 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 9/38:31 pm
BOS
- GCM
2 stops40h 54m
United Airlines
Deal found 7/5![United Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 7/5. 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 8/36:05 pm
BOS
- GCM
2 stops19h 25m
United Airlines
Deal found 7/5![United Airlines logo]()
$151
This United Airlines deal was found by Cheapflights users on 7/6. 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 11/117:25 am
BOS
- GCM
1 stop9h 05m
United Airlines
Deal found 7/6![United Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 7/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:15 pm
BOS
- GCM
2 stops14h 40m
Southwest
Deal found 7/3![Southwest logo]()
$166
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 July 7, 2026.
Round-trip from | $343 (Delta) |
|---|---|
One-way from | $119 (Delta) |
Popular in | December |
Cheapest in | January |
Average price | $544 |
Good round-trip deal | $3,288 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 July 7, 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
Fri 8/28
5:30 am-11:39 am
1 stop7h 09m
George Town Owen Roberts Intl
Mon 8/31
1:04 pm-11:41 pm
1 stop9h 37m
$343
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 11/14
6:00 am-4:35 pm
2 stops10h 35m
George Town Owen Roberts Intl
Sat 11/21
2:50 pm-11:22 pm
1 stop8h 32m
$343
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Tue 8/25
5:30 am-11:39 am
1 stop7h 09m
George Town Owen Roberts Intl
Tue 9/1
1:04 pm-11:41 pm
1 stop9h 37m
$343
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sat 8/29
5:30 am-11:39 am
1 stop7h 09m
George Town Owen Roberts Intl
Mon 8/31
1:04 pm-11:41 pm
1 stop9h 37m
$343
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 8/21
8:31 pm-12:25 pm
2 stops16h 54m
George Town Owen Roberts Intl
Sat 8/29
1:35 pm-9:36 am
2 stops19h 01m
$352
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Thu 10/1
8:31 pm-12:25 pm
2 stops40h 54m
George Town Owen Roberts Intl
Sun 10/4
1:35 pm-11:39 pm
1 stop9h 04m
$362
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Mon 11/9
9:00 pm-12:35 pm
2 stops15h 35m
George Town Owen Roberts Intl
Wed 11/11
1:30 pm-8:05 am
2 stops18h 35m
$392
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Fri 8/21
5:30 am-11:39 am
1 stop7h 09m
George Town Owen Roberts Intl
Tue 8/25
1:04 pm-11:41 pm
1 stop9h 37m
$455
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Wed 7/29
8:15 pm-12:30 pm
2 stops17h 15m
George Town Owen Roberts Intl
Tue 8/4
1:35 pm-11:30 pm
1 stop8h 55m
$457
BostonGeorge Town
BOS - GCM
BOSGCM
Boston Logan Intl
Sun 1/3
6:00 am-4:35 pm
1 stop10h 35m
George Town Owen Roberts Intl
Thu 1/7
2:50 pm-9:24 am
1 stop18h 34m
$464
Showing 1-10 of 22 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 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.
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 July 7, 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.
Comfort
7.8
Entertainment
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Overall
7.8
Food
7.2
Boarding
8.1
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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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 July 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$386 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$315 | Average$534 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$331 | Average$550 | FlexibilityNo cancel fee | On-time71% |