$588+ Cheap flights from New Haven (HVN) to the Cayman Islands
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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — GCM
Nov 29 — Dec 61
1 adult, Economy
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1. Tell us where you want to go
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Cheapest flights from New Haven to Cayman IslandsExplore the most affordable flight options available from New Haven to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.
Explore the most affordable flight options available from New Haven to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:00 amHVN - GCM
1 stop10h 20mMultiple Airlines
Sun 12/212:40 pmGCM - HVN
2 stops22h 02mMultiple Airlines
Deal found 10/30![Multiple Airlines logo]()
$588
Cheap flight deals from New Haven to Cayman Islands
Keep the following information in mind while searching for New Haven to Cayman Islands flight deals. Data was last updated October 30, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $588 (Mytrip) |
Popular in | December |
Cheapest in | March |
Average price | $396 |
Cheapflights Fare Finder
Customize your flight search to find flights from New Haven 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 October 30, 2025.
Use the filters below to find and compare flights from New Haven to the Cayman Islands that are best for you.
Fly from
New Haven
Fly to
Cayman Islands
Route
Depart
Return
Price
New HavenGeorge Town
HVN - GCM
HVNGCM
Tweed-New Haven
Sun 12/14
7:00 am-5:20 pm
1 stop10h 20m
George Town Owen Roberts Intl
Sun 12/21
2:40 pm-12:42 pm
2 stops22h 02m
$588
Best time to book a flight from New Haven to Cayman Islands
Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from New Haven with our price prediction graph.
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 New Haven to the Cayman Islands
What is the cheapest month to book a flight from New Haven to Cayman Islands?
Currently, October is the cheapest month in which you can book a flight from New Haven to Cayman Islands (average of $119). Flying from New Haven to Cayman Islands in June is currently the most expensive (average of $348). 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.