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Cayman Islands

$124+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — GCM
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 April 2, 2025.

Round-trip from

$337
(JetBlue Airways)

One-way from

$124
(Southwest)
From Connecticut to Cayman Islands
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One-way flight from Connecticut to Cayman Islands
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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 April 2, 2025.

This JetBlue Airways deal was found by Cheapflights users on 4/2. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:39 amJFK - GCM
Nonstop4h 01mJetBlue
Sat 5/1711:40 amGCM - JFK
Nonstop3h 54mJetBlue
Deal found 4/2$337
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 5/175:55 amEWR - GCM
1 stop8h 35mUnited Airlines
Sat 5/242:40 pmGCM - EWR
Nonstop3h 56mUnited Airlines
Deal found 4/1$342
This Gotogate deal was found by Cheapflights users on 4/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/710:45 amJFK - GCM
Nonstop4h 00mCayman Airways
Sun 9/146:10 pmGCM - JFK
Nonstop3h 50mCayman Airways
Deal found 4/2$348
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/266:00 amJFK - GCM
1 stop6h 22mDelta
Wed 4/3012:47 pmGCM - JFK
1 stop8h 43mDelta
Deal found 4/2$352
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/265:59 amEWR - GCM
1 stop6h 23mDelta
Wed 4/3012:47 pmGCM - EWR
1 stop9h 15mDelta
Deal found 4/2$352
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:00 amLGA - GCM
1 stop6h 35mAmerican Airlines
Mon 5/512:25 pmGCM - LGA
1 stop9h 05mAmerican Airlines
Deal found 4/1$352
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/268:09 amJFK - GCM
1 stop7h 06mAmerican Airlines
Mon 5/122:10 pmGCM - JFK
2 stops16h 42mAmerican Airlines
Deal found 4/2$356
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/265:30 pmEWR - GCM
2 stops19h 05mAmerican Airlines
Sat 5/32:55 pmGCM - EWR
2 stops18h 26mAmerican Airlines
Deal found 4/2$356
This Priceline deal was found by Cheapflights users on 4/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/79:00 amJFK - GCM
2 stops27h 55mMultiple Airlines
Sun 9/146:10 pmGCM - JFK
Nonstop3h 50mMultiple Airlines
Deal found 4/2$393
This Gotogate deal was found by Cheapflights users on 4/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/36:00 amLGA - GCM
1 stop8h 30mAir Canada
Sun 4/62:35 pmGCM - LGA
1 stop16h 16mAir Canada
Deal found 4/1$395
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:30 amLGA - GCM
2 stops9h 20mSouthwest
Thu 6/512:45 pmGCM - LGA
2 stops22h 15mSouthwest
Deal found 4/1$405
This Air Canada deal was found by Cheapflights users on 4/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/36:30 amEWR - GCM
1 stop8h 00mAir Canada
Tue 4/82:30 pmGCM - EWR
1 stop16h 39mAir Canada
Deal found 4/1$410

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 April 2, 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

Sat 5/10

7:39 am-10:40 am

Nonstop4h 01m

George Town Owen Roberts Intl

Sat 5/17

11:40 am-4:34 pm

Nonstop3h 54m

$337

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Sat 5/17

5:55 am-1:30 pm

1 stop8h 35m

George Town Owen Roberts Intl

Sat 5/24

2:40 pm-7:36 pm

Nonstop3h 56m

$342

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sun 9/7

10:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 9/14

6:10 pm-11:00 pm

Nonstop3h 50m

$348

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sat 4/26

6:00 am-11:22 am

1 stop6h 22m

George Town Owen Roberts Intl

Wed 4/30

12:47 pm-10:30 pm

1 stop8h 43m

$352

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

Thu 5/1

6:00 am-11:35 am

1 stop6h 35m

George Town Owen Roberts Intl

Mon 5/5

12:25 pm-10:30 pm

1 stop9h 05m

$352

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Sat 4/26

5:59 am-11:22 am

1 stop6h 23m

George Town Owen Roberts Intl

Wed 4/30

12:47 pm-11:02 pm

1 stop9h 15m

$352

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sat 4/26

8:09 am-2:15 pm

1 stop7h 06m

George Town Owen Roberts Intl

Mon 5/12

2:10 pm-7:52 am

2 stops16h 42m

$356

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Sat 4/26

5:30 pm-11:35 am

2 stops19h 05m

George Town Owen Roberts Intl

Sat 5/3

2:55 pm-10:21 am

2 stops18h 26m

$356

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Sun 9/7

9:00 am-11:55 am

2 stops27h 55m

George Town Owen Roberts Intl

Sun 9/14

6:10 pm-11:00 pm

Nonstop3h 50m

$393

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

Sat 5/31

6:30 am-2:50 pm

2 stops9h 20m

George Town Owen Roberts Intl

Thu 6/5

12:45 pm-12:00 pm

2 stops22h 15m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 47 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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. 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 Cayman Islands. Reviews last updated April 2, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Connecticut to Cayman Islands 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.
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,616 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Overall

8.0

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $124. However, be on the lookout for offers from JetBlue and Delta, 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

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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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Top 4 airlines flying from Connecticut to Cayman Islands

Discover the top 4 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$440Average$546FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$471Average$571FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$485Average$704FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$529Average$575FlexibilityNo cancel feeOn-time69%

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