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Cayman Islands

$115+ Cheap flights from Connecticut 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — GCM
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Connecticut to Cayman Islands

Keep the following information in mind while searching for Connecticut to Cayman Islands flight deals. Data was last updated September 15, 2025.

Round-trip from

$313
(flygcity.se)

One-way from

$115
(JetBlue)

Popular in

December

Cheapest in

July

Average price

$589
From Connecticut to Cayman Islands
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One-way flight from Connecticut to Cayman Islands
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Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Connecticut to Cayman Islands

Cheapest flights from Connecticut to Cayman Islands
Explore the most affordable flight options available from Connecticut to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This flygcity.se deal was found by Cheapflights users on 9/13. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:45 amJFK - GCM
Nonstop4h 00mJetBlue
Sat 10/1111:45 amGCM - JFK
Nonstop3h 44mJetBlue
Deal found 9/13$313
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:35 amJFK - GCM
Nonstop3h 56mJetBlue
Thu 11/133:45 pmGCM - JFK
Nonstop3h 47mJetBlue
Deal found 9/15$329
This United Airlines deal was found by Cheapflights users on 9/13. 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 11/299:10 amEWR - GCM
Nonstop4h 05mUnited Airlines
Sat 12/62:25 pmGCM - EWR
Nonstop3h 52mUnited Airlines
Deal found 9/13$329
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 11/135:45 amEWR - GCM
1 stop10h 45mUnited Airlines
Sun 11/162:25 pmGCM - EWR
Nonstop3h 52mUnited Airlines
Deal found 9/13$334
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:22 amJFK - GCM
1 stop7h 33mJetBlue
Sun 12/73:40 pmGCM - JFK
Nonstop3h 47mJetBlue
Deal found 9/14$337
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Sun 10/269:10 amEWR - GCM
Nonstop4h 05mUnited Airlines
Tue 10/284:45 pmGCM - EWR
1 stop16h 40mUnited Airlines
Deal found 9/14$339
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2911:08 amJFK - GCM
Nonstop3h 51mJetBlue
Sat 12/63:55 pmGCM - JFK
1 stop7h 43mJetBlue
Deal found 9/13$342
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:33 amJFK - GCM
1 stop5h 52mAmerican Airlines
Wed 9/2412:25 pmGCM - JFK
1 stop8h 11mAmerican Airlines
Deal found 9/13$344
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:30 amEWR - GCM
1 stop12h 50mAmerican Airlines
Tue 11/48:45 amGCM - EWR
1 stop12h 27mAmerican Airlines
Deal found 9/13$344
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:30 amLGA - GCM
1 stop5h 55mAmerican Airlines
Mon 9/2212:10 pmGCM - LGA
1 stop9h 50mAmerican Airlines
Deal found 9/13$344
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sun 9/146:30 pmJFK - GCM
1 stop17h 40mAmerican Airlines
Wed 9/1712:25 pmGCM - JFK
1 stop8h 11mAmerican Airlines
Deal found 9/14$345
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/295:59 amEWR - GCM
1 stop6h 11mAmerican Airlines
Wed 11/51:05 pmGCM - EWR
1 stop7h 20mAmerican Airlines
Deal found 9/14$345

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut 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 September 15, 2025.
Use the filters below to find and compare flights from Connecticut to the Cayman Islands that are best for you.

Fly from

Connecticut

Fly to

Cayman Islands

Route

Depart

Return

Price

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sun 11/9

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

Sat 11/15

3:45 pm-7:32 pm

Nonstop3h 47m

$329

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Sat 11/29

9:10 am-1:15 pm

Nonstop4h 05m

George Town Owen Roberts Intl

Sat 12/6

2:25 pm-6:17 pm

Nonstop3h 52m

$329

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Fri 11/14

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

Sat 11/15

3:45 pm-7:32 pm

Nonstop3h 47m

$329

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sun 11/9

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

Fri 11/14

3:45 pm-7:32 pm

Nonstop3h 47m

$329

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Wed 11/12

7:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sun 11/16

2:25 pm-6:17 pm

Nonstop3h 52m

$334

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Thu 12/4

7:10 am-4:30 pm

1 stop9h 20m

George Town Owen Roberts Intl

Sun 12/7

2:25 pm-6:17 pm

Nonstop3h 52m

$334

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Thu 11/13

6:30 am-2:46 pm

1 stop8h 16m

George Town Owen Roberts Intl

Mon 11/17

12:55 pm-8:30 pm

1 stop7h 35m

$344

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Fri 10/3

6:33 am-11:25 am

1 stop5h 52m

George Town Owen Roberts Intl

Fri 10/10

12:10 pm-12:25 am

1 stop11h 15m

$344

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Fri 10/31

5:00 am-11:20 am

1 stop7h 20m

George Town Owen Roberts Intl

Fri 11/7

12:55 pm-10:05 pm

1 stop9h 10m

$344

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Fri 10/31

5:45 am-3:30 pm

1 stop10h 45m

George Town Owen Roberts Intl

Mon 11/3

5:45 pm-10:25 am

1 stop16h 40m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 53 results
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Best time to book a flight from Connecticut to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Connecticut 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 Connecticut to the Cayman Islands

What is the cheapest month to book a flight from Connecticut to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Connecticut to Cayman Islands (average of $467). Flying from Connecticut to Cayman Islands in March is currently the most expensive (average of $594). 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.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Cayman Islands?

    For as low as $329, JetBlue can have you in Cayman Islands from Connecticut in 3h 56m. The distance from Connecticut to Cayman Islands is about 1540 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Connecticut to Cayman Islands one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $115. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Connecticut to Cayman Islands for a low price.

  • Can I find deals for flights from Connecticut to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Connecticut to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Cayman Islands.

  • Can I find deals for business class flights from Connecticut to Cayman Islands?

    Yes. Cheapflights offers flight deals from Connecticut to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Connecticut to Cayman Islands (average of $467). Flying from Connecticut to Cayman Islands in March is currently the most expensive (average of $594). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Connecticut to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Montego Bay flights
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O'Hare Intl to Punta Cana flights
Atlanta to Punta Cana flights

Top 3 airlines flying from Connecticut to Cayman Islands

Discover the top 3 airlines that operate flights from Connecticut 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$440Average$558FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$463Average$567FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$485Average$704FlexibilityNo cancel feeOn-time63%

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