$128+ Cheap flights from Boston (BOS) to Grand Cayman
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Oct 4 — Oct 111
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Grand Cayman 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Grand Cayman
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Best
Last-minute
One-way
Cheapest flights from Boston to Grand CaymanExplore the most affordable flight options available from Boston to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
Explore the most affordable flight options available from Boston to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 4, 2026.
This Expedia deal was found by Cheapflights users on 8/30. 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 10/27:05 pm -
1 stop15h 40m
Mon 10/512:25 pm -
1 stop26h 40m
Deal found 8/30![Air Canada logo]()
$361
This Expedia deal was found by Cheapflights users on 8/30. 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.
Sat 9/196:50 pm -
2 stops41h 35m
Sat 9/2610:40 am -
1 stop11h 00m
Deal found 8/30![Air Canada logo]()
$364
This Air Canada deal was found by Cheapflights users on 8/31. 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 9/103:35 pm -
2 stops43h 10m
Mon 9/1412:25 pm -
1 stop9h 15m
Deal found 8/31![Air Canada logo]()
$374
This Orbitz deal was found by Cheapflights users on 9/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:40 pm -
1 stop16h 30m
Sun 11/11:10 pm -
1 stop9h 27m
Deal found 9/3![Air Canada logo]()
$375
This Travelocity deal was found by Cheapflights users on 9/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:35 pm -
2 stops43h 10m
Mon 9/2112:25 pm -
1 stop28h 39m
Deal found 9/1![Air Canada logo]()
$384
This Expedia deal was found by Cheapflights users on 8/30. 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.
Sat 10/2410:50 am -
1 stop25h 20m
Sat 10/3112:10 pm -
1 stop22h 12m
Deal found 8/30![Air Canada logo]()
$389
Best flights from Boston to Grand CaymanDiscover carefully curated flight deals from Boston to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Boston to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. 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 -
2 stops10h 35m
Sat 11/215:10 pm -
1 stop6h 49m
Deal found 8/31![United Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/30. 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 9/195:30 am -
1 stop7h 10m
Sat 9/261:05 pm -
1 stop11h 12m
Deal found 8/30![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 2/204:00 pm -
2 stops20h 55m
Sat 2/271:25 pm -
2 stops9h 35m
Deal found 8/31![Southwest logo]()
$527
This United Airlines deal was found by Cheapflights users on 8/31. 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 12/45:45 am -
2 stops10h 45m
Tue 12/85:45 pm -
2 stops22h 08m
Deal found 8/31![United Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 12/225:45 am -
2 stops10h 50m
Mon 12/285:10 pm -
1 stop6h 49m
Deal found 9/3![United Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/30. 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 11/55:30 am -
2 stops11h 00m
Mon 11/95:45 pm -
2 stops19h 01m
Deal found 8/30![United Airlines logo]()
$465
This United Airlines deal was found by Cheapflights users on 8/30. 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 1/226:00 am -
1 stop7h 45m
Sat 1/305:45 pm -
1 stop18h 35m
Deal found 8/30![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 9/1. 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 2/164:30 pm -
2 stops21h 15m
Wed 2/242:55 pm -
1 stop18h 29m
Deal found 9/1![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 8/31. 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 11/47:15 am -
1 stop9h 15m
Fri 11/65:45 pm -
1 stop18h 40m
Deal found 8/31![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 9/1. 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 2/187:35 pm -
2 stops21h 00m
Wed 2/242:55 pm -
1 stop18h 29m
Deal found 9/1![United Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Sat 2/204:30 pm -
2 stops21h 15m
Sat 2/275:30 pm -
1 stop17h 01m
Deal found 9/2![United Airlines logo]()
$521
Last-minute flights from Boston to Grand CaymanDiscover last-minute flight deals from Boston to Grand Cayman. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Grand Cayman. Data last updated September 4, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/31. 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 9/103:35 pm -
2 stops43h 10m
Mon 9/1412:25 pm -
1 stop9h 15m
Deal found 8/31![Air Canada logo]()
$374
This Travelocity deal was found by Cheapflights users on 9/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:35 pm -
2 stops43h 10m
Mon 9/2112:25 pm -
1 stop28h 39m
Deal found 9/1![Air Canada logo]()
$384
This Expedia deal was found by Cheapflights users on 8/30. 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.
Sat 9/196:50 pm -
2 stops41h 35m
Sat 9/2610:40 am -
1 stop11h 00m
Deal found 8/30![Air Canada logo]()
$364
This Expedia deal was found by Cheapflights users on 8/30. 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 10/27:05 pm -
1 stop15h 40m
Mon 10/512:25 pm -
1 stop26h 40m
Deal found 8/30![Air Canada logo]()
$361
This Expedia deal was found by Cheapflights users on 8/30. 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.
Sat 10/2410:50 am -
1 stop25h 20m
Sat 10/3112:10 pm -
1 stop22h 12m
Deal found 8/30![Air Canada logo]()
$389
This Orbitz deal was found by Cheapflights users on 9/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:40 pm -
1 stop16h 30m
Sun 11/11:10 pm -
1 stop9h 27m
Deal found 9/3![Air Canada logo]()
$375
One-way flights from Boston to Grand CaymanSearch for one-way flight options from Boston to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Boston to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This Travelocity deal was found by Cheapflights users on 9/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:50 pm -
2 stops41h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Air Canada logo]()
$128
This American Airlines deal was found by Cheapflights users on 9/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:00 am -
1 stop14h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$129
This Air Canada deal was found by Cheapflights users on 9/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:55 pm -
1 stop17h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Air Canada logo]()
$130
This Orbitz deal was found by Cheapflights users on 8/30. 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.
Sat 9/126:50 pm -
2 stops41h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/30![Air Canada logo]()
$134
This Air Canada deal was found by Cheapflights users on 8/31. 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 9/2710:50 am -
1 stop25h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Air Canada logo]()
$136
This Air Canada deal was found by Cheapflights users on 9/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2111:15 am -
1 stop24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Air Canada logo]()
$138
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:50 am -
1 stop23h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Air Canada logo]()
$141
This Air Canada deal was found by Cheapflights users on 9/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3011:15 am -
1 stop24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Air Canada logo]()
$143
This American Airlines deal was found by Cheapflights users on 8/31. 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 2/285:00 am -
1 stop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![American Airlines logo]()
$144
Find flight deals from Boston to Grand Cayman
Keep the following information in mind while searching for Boston to Grand Cayman flight deals. Data was last updated September 4, 2026.
Round-trip from | $361 (Expedia) |
|---|---|
One-way from | $128 (Travelocity) |
Popular in | December |
Cheapest in | January |
Average price | $452 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Grand Cayman 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 September 4, 2026.
Use the filters below to find and compare flights from Boston to Grand Cayman 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 10/28
7:17 pm-11:40 am
1 stop17h 23m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Mon 3/1
8:15 pm-12:40 pm
1 stop16h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Thu 10/1
8:57 pm-11:40 am
1 stop15h 43m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 10/31
3:41 pm-4:30 pm
3 stops25h 49m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$210
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sun 2/28
6:00 am-4:35 pm
2 stops10h 35m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Quickest round-trip
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Wed 11/4
7:15 am-4:30 pm
1 stop9h 15m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Tue 11/3
3:41 pm-4:30 pm
3 stops24h 49m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$220
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 10/3
10:07 am-12:30 pm
1 stop27h 23m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$223
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Tue 3/2
6:00 am-1:45 pm
3 stops31h 45m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$231
BostonGeorge Town
BOS Boston Logan Intl - GCM George Town Owen Roberts Intl
BOSGCM
Boston Logan Intl
Sat 11/14
6:00 am-4:35 pm
2 stops10h 35m
George Town Owen Roberts Intl
Sat 11/21
5:10 pm-11:59 pm
1 stop6h 49m
$393
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Boston to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from Boston with our price prediction graph.
BOS-GCM
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 Grand Cayman
BOS-zzLAW
BOS-GCM
What is the cheapest month to book a flight from Boston to Grand Cayman?
Currently, January is the cheapest month in which you can book a flight from Boston to Grand Cayman (average of $374). Flying from Boston to Grand Cayman in December is currently the most expensive (average of $675). 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 Grand Cayman?
The price you pay for your flight from Boston to Grand Cayman may vary depending on when you book. For the best chance of a lower fare, look to book 47 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Grand Cayman
Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated September 4, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Boston to Grand Cayman have to say. 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
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Comfort
7.8
Food
7.2
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 Grand Cayman. 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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Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Grand Cayman by cabin class
Find flights from Boston to Grand Cayman, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Grand Cayman flights
Browse other Boston and Grand Cayman flight options. Last updated on September 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Boston to Grand Cayman
Discover the top 4 airlines that operate flights from Boston to Grand Cayman. 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 September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$506 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$236 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$547 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$331 | Average$565 | FlexibilityNo cancel fee | On-time71% |