$225+ Cheap flights from the Cayman Islands to Boston (BOS)
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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — BOS
Nov 18 — Nov 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Cayman Islands to Boston with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Cayman Islands to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Cayman Islands to BostonExplore the most affordable flight options available from Cayman Islands to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
Explore the most affordable flight options available from Cayman Islands to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:45 pm -
2 stops25h 29m
Mon 11/237:41 pm -
2 stops20h 49m
Deal found 10/17![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/122:55 pm -
2 stops19h 24m
Mon 12/148:25 pm -
2 stops20h 05m
Deal found 10/17![United Airlines logo]()
$386
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:25 pm -
1 stop26h 40m
Tue 10/275:45 am -
1 stop30h 25m
Deal found 10/19![Air Canada logo]()
$417
This Travelocity deal was found by Cheapflights users on 10/15. 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.
Fri 11/201:10 pm -
1 stop9h 27m
Wed 11/255:45 am -
1 stop30h 25m
Deal found 10/15![Air Canada logo]()
$425
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/205:45 pm -
2 stops31h 01m
Wed 11/256:00 am -
3 stops34h 30m
Deal found 10/15![United Airlines logo]()
$428
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:25 pm -
1 stop9h 15m
Mon 10/266:35 pm -
2 stops41h 35m
Deal found 10/19![Air Canada logo]()
$430
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:25 pm -
1 stop28h 49m
Sat 10/246:00 am -
1 stop30h 10m
Deal found 10/18![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:25 pm -
2 stops25h 16m
Wed 10/2810:40 am -
2 stops49h 30m
Deal found 10/17![Air Canada logo]()
$448
This Air Canada deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2512:10 pm -
1 stop19h 44m
Tue 10/275:45 am -
1 stop30h 25m
Deal found 10/19![Air Canada logo]()
$450
Best flights from Cayman Islands to BostonDiscover carefully curated flight deals from Cayman Islands to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
Discover carefully curated flight deals from Cayman Islands to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/205:45 pm -
2 stops30h 13m
Wed 11/256:36 pm -
2 stops21h 54m
Deal found 10/15![United Airlines logo]()
$369
This Travelocity deal was found by Cheapflights users on 10/15. 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.
Fri 11/201:10 pm -
1 stop9h 27m
Wed 11/255:45 am -
1 stop30h 25m
Deal found 10/15![Air Canada logo]()
$425
This Mytrip deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:25 am -
3 stops22h 48m
Mon 12/146:35 pm -
2 stops17h 35m
Deal found 10/17![Multiple Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/193:11 pm -
1 stop8h 42m
Sat 3/208:45 am -
2 stops11h 03m
Deal found 10/14![American Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:10 pm -
1 stop6h 49m
Mon 12/1410:00 am -
2 stops30h 30m
Deal found 10/17![United Airlines logo]()
$386
This Mytrip deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
3 stops28h 30m
Mon 11/236:35 pm -
2 stops17h 35m
Deal found 10/17![Multiple Airlines logo]()
$711
This Air Canada deal was found by Cheapflights users on 10/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/201:10 pm -
1 stop21h 02m
Sat 3/207:40 pm -
1 stop16h 30m
Deal found 10/14![Air Canada logo]()
$1,015
This Orbitz deal was found by Cheapflights users on 10/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/201:10 pm -
1 stop21h 02m
Sat 3/2011:04 am -
Nonstop4h 28m
Deal found 10/14![Multiple Airlines logo]()
$1,093
Last-minute flights from Cayman Islands to BostonDiscover last-minute flight deals from Cayman Islands to Boston. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Cayman Islands to Boston. Data last updated October 19, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:25 am -
1 stop10h 15m
Tue 10/275:45 am -
1 stop30h 25m
Deal found 10/17![Air Canada logo]()
$417
This Air Canada deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:25 am -
1 stop10h 15m
Wed 10/2810:40 am -
2 stops49h 30m
Deal found 10/17![Air Canada logo]()
$430
This United Airlines deal was found by Cheapflights users on 10/14. 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 10/241:35 pm -
2 stops18h 43m
Mon 10/263:41 pm -
3 stops24h 49m
Deal found 10/14![United Airlines logo]()
$540
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2512:10 pm -
1 stop19h 44m
Tue 10/275:45 am -
1 stop30h 25m
Deal found 10/18![Air Canada logo]()
$450
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:25 pm -
2 stops19h 54m
Wed 10/284:38 pm -
2 stops23h 52m
Deal found 10/18![United Airlines logo]()
$453
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2512:10 pm -
1 stop19h 44m
Mon 10/266:35 pm -
2 stops41h 35m
Deal found 10/18![Air Canada logo]()
$470
One-way flights from Cayman Islands to BostonSearch for one-way flight options from Cayman Islands to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
Search for one-way flight options from Cayman Islands to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This JetBlue deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:10 pm -
1 stop8h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![JetBlue logo]()
$225
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Wed 11/115:45 pm -
2 stops22h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:23 am -
1 stop7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/221:13 pm -
1 stop10h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:45 pm -
2 stops31h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![United Airlines logo]()
$243
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/165:45 pm -
2 stops23h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$244
This United Airlines deal was found by Cheapflights users on 10/14. 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 11/145:10 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:10 pm -
2 stops24h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![United Airlines logo]()
$254
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:25 am -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$258
This American Airlines deal was found by Cheapflights users on 10/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/177:21 am -
1 stop14h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![American Airlines logo]()
$259
Find flight deals from Cayman Islands to Boston
Keep the following information in mind while searching for Cayman Islands to Boston flight deals. Data was last updated October 19, 2026.
Round-trip from | $369 (United Airlines) |
|---|---|
One-way from | $225 (JetBlue) |
Popular in | April |
Cheapest in | February |
Average price | $534 |
Cheapflights Fare Finder
Customize your flight search to find flights from Cayman Islands to Boston 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 October 19, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Thu 11/12
5:45 pm-1:31 pm
2 stops19h 46m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Mon 11/16
8:23 am-12:59 am
1 stop16h 36m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Thu 12/31
5:45 pm-1:18 am
2 stops31h 33m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$243
Quickest round-trip
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Sat 11/21
2:50 pm-11:47 pm
1 stop8h 57m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Sun 12/20
2:25 pm-6:27 pm
1 stop28h 02m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Sat 12/5
2:25 pm-9:51 am
1 stop19h 26m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Sat 12/12
5:45 pm-4:45 pm
1 stop23h 00m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$254
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Fri 11/20
5:45 pm-11:58 pm
2 stops30h 13m
Boston Logan Intl
Wed 11/25
6:36 pm-4:30 pm
2 stops21h 54m
$369
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Sat 12/12
5:10 pm-11:59 pm
1 stop6h 49m
Boston Logan Intl
Mon 12/14
10:00 am-4:30 pm
2 stops30h 30m
$386
George TownBoston
GCM George Town Owen Roberts Intl - BOS Boston Logan Intl
GCMBOS
George Town Owen Roberts Intl
Fri 11/20
1:10 pm-10:37 pm
1 stop9h 27m
Boston Logan Intl
Wed 11/25
5:45 am-12:10 pm
1 stop30h 25m
$425
Showing 1-10 of 15 resultsSorted by cheapest first
Best time to book a flight from Cayman Islands to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Cayman Islands with our price prediction graph.
GCM-BOS
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 the Cayman Islands to Boston
KY0-BOS
GCM-BOS
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated October 19, 2026.
Peruse reviews from past customers who have flown with JetBlue and American Airlines from the Cayman Islands to Boston 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.
Crew
7.9
Food
6.6
Entertainment
7.1
Boarding
7.3
Overall
7.1
Comfort
7.4
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Crew
7.9
Food
6.6
Entertainment
7.1
Boarding
7.3
Overall
7.1
Comfort
7.4
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Crew
7.9
Food
6.6
Entertainment
7.1
Boarding
7.3
Overall
7.1
Comfort
7.4
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Related info for your journey
Find useful and relevant information for your journey from Cayman Islands to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Boston flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Cayman Islands to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Cayman Islands to Boston by cabin class
Find flights from Cayman Islands to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cayman Islands and Boston flights
Browse other Cayman Islands and Boston flight options. Last updated on October 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Cayman Islands to Boston
Discover the top 2 airlines that operate flights from Cayman Islands to Boston. 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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$265 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$302 | Average$535 | FlexibilityNo cancel fee | On-time71% |