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Cayman Islands

$138+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — GCM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$372
(American Airlines)

One-way from

$138
(American Airlines)
From Connecticut to Cayman Islands
Search Deals
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 May 1, 2025.

This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:00 amJFK - GCM
Nonstop4h 00mCayman Airways
Sun 11/95:10 pmGCM - JFK
Nonstop4h 50mCayman Airways
Deal found 4/30$355
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/109:30 pmJFK - GCM
2 stops14h 45mAmerican Airlines
Thu 6/192:05 pmGCM - JFK
1 stop7h 45mAmerican Airlines
Deal found 4/30$372
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 6/145:00 amEWR - GCM
1 stop5h 55mAmerican Airlines
Tue 6/1712:10 pmGCM - EWR
1 stop9h 54mAmerican Airlines
Deal found 5/1$380
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/67:15 pmLGA - GCM
1 stop15h 40mAmerican Airlines
Wed 6/112:05 pmGCM - LGA
1 stop8h 40mAmerican Airlines
Deal found 4/30$380
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/116:00 amJFK - GCM
1 stop6h 25mDelta
Wed 6/1812:40 pmGCM - JFK
1 stop8h 43mDelta
Deal found 4/30$405
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 7/36:00 amLGA - GCM
1 stop6h 25mDelta
Tue 7/812:40 pmGCM - LGA
1 stop6h 46mDelta
Deal found 4/29$405
This Air Canada deal was found by Cheapflights users on 5/1. 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 6/56:00 amLGA - GCM
1 stop6h 55mAir Canada
Mon 6/912:50 pmGCM - LGA
2 stops18h 13mAir Canada
Deal found 5/1$424
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/113:35 pmJFK - GCM
1 stop21h 20mAir Canada
Mon 6/1612:50 pmGCM - JFK
2 stops31h 58mAir Canada
Deal found 4/30$434
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/275:44 amBDL - GCM
1 stop8h 26mAmerican Airlines
Fri 6/62:05 pmGCM - BDL
2 stops17h 57mAmerican Airlines
Deal found 4/30$438
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:00 amPVD - GCM
1 stop6h 25mDelta
Tue 7/812:40 pmGCM - PVD
1 stop10h 21mDelta
Deal found 4/30$459
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/186:00 amBDL - GCM
1 stop6h 25mDelta
Fri 7/2512:40 pmGCM - BDL
1 stop8h 41mDelta
Deal found 4/30$459
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 7/44:29 pmPVD - GCM
2 stops18h 21mAmerican Airlines
Wed 8/1312:10 pmGCM - PVD
2 stops10h 08mAmerican Airlines
Deal found 5/1$463

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 May 1, 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

Tue 6/10

9:30 pm-11:15 am

2 stops14h 45m

George Town Owen Roberts Intl

Thu 6/19

2:05 pm-10:50 pm

1 stop7h 45m

$372

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

Sat 6/14

5:00 am-9:55 am

1 stop5h 55m

George Town Owen Roberts Intl

Thu 6/19

12:10 pm-12:29 am

1 stop11h 19m

$380

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

Fri 6/6

7:15 pm-9:55 am

1 stop15h 40m

George Town Owen Roberts Intl

Wed 6/11

12:10 pm-8:59 pm

1 stop7h 49m

$380

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Wed 6/11

6:00 am-11:25 am

1 stop6h 25m

George Town Owen Roberts Intl

Wed 6/18

12:40 pm-10:23 pm

1 stop8h 43m

$405

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

Thu 7/3

6:00 am-11:25 am

1 stop6h 25m

George Town Owen Roberts Intl

Tue 7/8

12:40 pm-8:26 pm

1 stop6h 46m

$405

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Thu 9/18

10:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sun 9/21

6:10 pm-11:00 pm

Nonstop3h 50m

$409

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

Thu 6/5

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Mon 6/9

12:50 pm-8:03 am

2 stops18h 13m

$424

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

Wed 6/11

3:35 pm-11:55 am

1 stop21h 20m

George Town Owen Roberts Intl

Mon 6/16

12:50 pm-9:48 pm

2 stops31h 58m

$434

HartfordGeorge Town

BDL - GCM

BDLGCM

Hartford Bradley Intl

Tue 5/27

5:44 am-1:10 pm

1 stop8h 26m

George Town Owen Roberts Intl

Fri 6/6

2:05 pm-9:02 am

2 stops17h 57m

$438

ProvidenceGeorge Town

PVD - GCM

PVDGCM

Providence-TFGreen

Fri 7/4

6:00 am-11:25 am

1 stop6h 25m

George Town Owen Roberts Intl

Tue 7/8

12:40 pm-12:01 am

1 stop10h 21m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 52 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 May 1, 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
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 American Airlines, with whom users have recently found tickets for as low as $138. However, be on the lookout for offers from Delta and Air Canada, 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 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$440Average$558FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$446Average$584FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$485Average$704FlexibilityNo cancel feeOn-time63%

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