Cayman Islands

$101+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — GCM
nov. 7 — nov. 141
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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 octubre 8, 2025.

Round-trip from

$261
(SmartFares)

One-way from

$101
(JetBlue)

Popular in

October

Cheapest in

July

Average price

$704
From Connecticut to Cayman Islands
One-way flight from Connecticut to Cayman Islands
Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in October 2025

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 octubre 8, 2025.

This SmartFares deal was found by Cheapflights users on 10/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:35 amJFK - GCM
Nonstop3h 56mJetBlue
jue. 11/63:45 pmGCM - JFK
Nonstop3h 47mJetBlue
Deal found 10/7$261
This Flysmarter deal was found by Cheapflights users on 10/6. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2710:35 amJFK - GCM
Nonstop3h 56mJetBlue
dom. 11/23:40 pmGCM - JFK
Nonstop3h 47mJetBlue
Deal found 10/6$276
This lastminute.com deal was found by Cheapflights users on 10/6. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2010:29 amJFK - GCM
Nonstop4h 02mJetBlue
jue. 11/273:43 pmGCM - JFK
Nonstop3h 46mJetBlue
Deal found 10/6$288
This Expedia deal was found by Cheapflights users on 10/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/910:35 amJFK - GCM
Nonstop3h 56mJetBlue
sáb. 11/153:45 pmGCM - JFK
Nonstop3h 47mJetBlue
Deal found 10/7$289
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/1410:35 amJFK - GCM
Nonstop3h 56mJetBlue
lun. 11/243:43 pmGCM - JFK
Nonstop3h 46mJetBlue
Deal found 10/7$290
This United Airlines deal was found by Cheapflights users on 10/6. 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.
sáb. 11/89:10 amEWR - GCM
Nonstop4h 05mUnited Airlines
sáb. 11/152:25 pmGCM - EWR
Nonstop3h 52mUnited Airlines
Deal found 10/6$290
This United Airlines deal was found by Cheapflights users on 10/6. 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.
jue. 12/115:45 amEWR - GCM
1 stop10h 45mUnited Airlines
dom. 12/142:25 pmGCM - EWR
Nonstop3h 52mUnited Airlines
Deal found 10/6$294
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:30 amJFK - GCM
1 stop5h 50mAmerican Airlines
jue. 11/63:36 pmGCM - JFK
1 stop6h 42mAmerican Airlines
Deal found 10/7$295
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/306:00 amLGA - GCM
1 stop6h 20mAmerican Airlines
jue. 11/63:10 pmGCM - LGA
1 stop7h 30mAmerican Airlines
Deal found 10/7$295
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/811:30 amJFK - GCM
1 stop8h 58mAmerican Airlines
mar. 11/119:00 amGCM - JFK
1 stop12h 19mAmerican Airlines
Deal found 10/7$304
This Delta deal was found by Cheapflights users on 10/7. 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.
jue. 10/306:00 amEWR - GCM
1 stop6h 40mDelta
jue. 11/62:00 pmGCM - EWR
1 stop9h 06mDelta
Deal found 10/7$304
This United Airlines deal was found by Cheapflights users on 10/6. 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.
jue. 10/306:00 amLGA - GCM
1 stop10h 30mUnited Airlines
mar. 11/45:45 pmGCM - LGA
1 stop17h 41mUnited Airlines
Deal found 10/6$304

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 octubre 8, 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

sáb. 11/8

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

sáb. 11/15

3:45 pm-7:32 pm

Nonstop3h 47m

$290

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

sáb. 11/8

9:10 am-1:15 pm

Nonstop4h 05m

George Town Owen Roberts Intl

sáb. 11/15

2:25 pm-6:17 pm

Nonstop3h 52m

$290

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

dom. 11/16

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

vie. 11/21

3:43 pm-7:29 pm

Nonstop3h 46m

$290

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

lun. 11/17

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

vie. 11/21

3:43 pm-7:29 pm

Nonstop3h 46m

$290

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

vie. 11/14

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

mar. 11/25

3:42 pm-7:29 pm

Nonstop3h 47m

$290

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

jue. 12/4

10:35 am-2:31 pm

Nonstop3h 56m

George Town Owen Roberts Intl

dom. 12/7

3:40 pm-7:27 pm

Nonstop3h 47m

$290

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

sáb. 11/22

7:30 am-11:30 am

Nonstop4h 00m

George Town Owen Roberts Intl

jue. 11/27

3:43 pm-7:29 pm

Nonstop3h 46m

$290

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

jue. 12/11

5:45 am-4:30 pm

1 stop10h 45m

George Town Owen Roberts Intl

dom. 12/14

2:25 pm-6:17 pm

Nonstop3h 52m

$294

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

vie. 10/31

6:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

mié. 11/5

1:05 pm-8:30 pm

1 stop7h 25m

$304

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

sáb. 11/8

7:00 am-3:00 pm

1 stop8h 00m

George Town Owen Roberts Intl

sáb. 11/22

3:18 pm-10:29 pm

1 stop7h 11m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 60 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, August is the cheapest month in which you can book a flight from Connecticut to Cayman Islands (average of $369). Flying from Connecticut to Cayman Islands in October is currently the most expensive (average of $601). 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 $290, 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 $101. However, be on the lookout for offers from Spirit 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, August is the cheapest month in which you can book a flight from Connecticut to Cayman Islands (average of $369). Flying from Connecticut to Cayman Islands in October is currently the most expensive (average of $601). 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.

Top 2 airlines flying from Connecticut to Cayman Islands

Discover the top 2 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 octubre 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$440Average$561FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$441Average$557FlexibilityNo cancel feeOn-time71%

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