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Cayman Islands

$109+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — GCM
jul. 30 — ago. 61
mié. 7/30
mié. 8/6
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 julio 25, 2025.

Round-trip from

$320
(United Airlines)

One-way from

$109
(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 julio 25, 2025.

This United Airlines deal was found by Cheapflights users on 7/24. 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. 10/256:00 amEWR - GCM
1 stop7h 30mUnited Airlines
sáb. 11/11:25 pmGCM - EWR
Nonstop3h 52mUnited Airlines
Deal found 7/24$320
This American Airlines deal was found by Cheapflights users on 7/24. 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.
lun. 9/88:00 pmJFK - GCM
1 stop16h 10mAmerican Airlines
vie. 9/1212:10 pmGCM - JFK
1 stop9h 11mAmerican Airlines
Deal found 7/24$330
This American Airlines deal was found by Cheapflights users on 7/24. 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.
mié. 8/275:00 amEWR - GCM
1 stop7h 20mAmerican Airlines
mar. 9/912:10 pmGCM - EWR
1 stop9h 44mAmerican Airlines
Deal found 7/24$330
This American Airlines deal was found by Cheapflights users on 7/24. 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.
mié. 8/276:00 amLGA - GCM
1 stop6h 20mAmerican Airlines
mar. 9/912:10 pmGCM - LGA
1 stop6h 48mAmerican Airlines
Deal found 7/24$330
This United Airlines deal was found by Cheapflights users on 7/24. 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.
dom. 11/166:00 amLGA - GCM
1 stop10h 30mUnited Airlines
mié. 11/195:45 pmGCM - LGA
1 stop28h 00mUnited Airlines
Deal found 7/24$340
This JetBlue deal was found by Cheapflights users on 7/22. 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.
sáb. 10/187:45 amJFK - GCM
Nonstop4h 00mJetBlue
sáb. 10/2511:45 amGCM - JFK
Nonstop3h 44mJetBlue
Deal found 7/22$347
This Trip.com deal was found by Cheapflights users on 7/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/169:00 amJFK - GCM
Nonstop4h 00mCayman Airways
mié. 11/195:10 pmGCM - JFK
Nonstop3h 50mCayman Airways
Deal found 7/23$352
This Delta deal was found by Cheapflights users on 7/22. 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.
mié. 11/196:00 amEWR - GCM
1 stop6h 37mDelta
dom. 11/232:02 pmGCM - EWR
1 stop10h 59mDelta
Deal found 7/22$356
This Air Canada deal was found by Cheapflights users on 7/22. 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.
mié. 10/87:55 pmEWR - GCM
1 stop17h 00mAir Canada
lun. 10/1312:50 pmGCM - EWR
1 stop8h 59mAir Canada
Deal found 7/22$377
This Priceline deal was found by Cheapflights users on 7/22. 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.
mié. 10/1510:30 amJFK - GCM
1 stop26h 25mMultiple Airlines
dom. 10/196:10 pmGCM - JFK
Nonstop3h 50mMultiple Airlines
Deal found 7/22$378
This American Airlines deal was found by Cheapflights users on 7/24. 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.
lun. 10/67:30 pmPVD - GCM
1 stop16h 50mAmerican Airlines
vie. 10/1012:25 pmGCM - PVD
1 stop9h 23mAmerican Airlines
Deal found 7/24$396
This Travelocity deal was found by Cheapflights users on 7/22. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/257:45 pmLGA - GCM
2 stops40h 35mAir Canada
vie. 11/281:30 pmGCM - LGA
1 stop28h 28mAir Canada
Deal found 7/22$411

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 julio 25, 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

lun. 9/8

8:00 pm-11:10 am

1 stop16h 10m

George Town Owen Roberts Intl

vie. 9/12

12:10 pm-10:21 pm

1 stop9h 11m

$330

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

mié. 8/27

5:00 am-11:20 am

1 stop7h 20m

George Town Owen Roberts Intl

mar. 9/9

12:10 pm-10:54 pm

1 stop9h 44m

$330

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

mié. 8/27

6:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

mar. 9/9

12:10 pm-7:58 pm

1 stop6h 48m

$330

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

sáb. 10/18

7:45 am-10:45 am

Nonstop4h 00m

George Town Owen Roberts Intl

sáb. 10/25

11:45 am-4:29 pm

Nonstop3h 44m

$347

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

jue. 9/18

11:45 am-2:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

sáb. 9/20

6:10 pm-11:00 pm

Nonstop3h 50m

$361

New YorkGeorge Town

LGA - GCM

LGAGCM

New York LaGuardia

sáb. 10/18

6:00 am-12:30 pm

1 stop7h 30m

George Town Owen Roberts Intl

sáb. 10/25

1:35 pm-11:14 pm

1 stop8h 39m

$370

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

mié. 8/13

7:37 pm-12:30 pm

1 stop17h 53m

George Town Owen Roberts Intl

dom. 8/17

1:35 pm-10:37 am

1 stop20h 02m

$376

NewarkGeorge Town

EWR - GCM

EWRGCM

Newark

mié. 10/8

7:55 pm-11:55 am

1 stop17h 00m

George Town Owen Roberts Intl

lun. 10/13

12:50 pm-10:49 pm

1 stop8h 59m

$377

New YorkGeorge Town

JFK - GCM

JFKGCM

New York John F Kennedy Intl

mié. 10/15

10:30 am-11:55 am

1 stop26h 25m

George Town Owen Roberts Intl

dom. 10/19

6:10 pm-11:00 pm

Nonstop3h 50m

$378

ProvidenceGeorge Town

PVD - GCM

PVDGCM

Providence-TFGreen

lun. 10/6

7:30 pm-11:20 am

1 stop16h 50m

George Town Owen Roberts Intl

vie. 10/10

12:25 pm-10:48 pm

1 stop9h 23m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 34 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 julio 25, 2025.
Read through reviews of airlines operating flights from Connecticut to the Cayman Islands, such as Porter Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Porter Airlines
8.0
Very good
314 reviews
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Southwest
8.0
Very good
4,235 reviews
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
Delta
8.0
Very good
7,967 reviews
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
United Airlines
7.4
Good
8,876 reviews
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
314 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Shawn,Jul 2025

EWR - YTZ

First time flying with porter and had an amazing experience. Will definitely use you guys whenever I get the chance. For context I had a flight from EWR to YTZ at 12:00pm. When I arrived early at 09:30 they put me on standby for the 10:00am, which I was able to make

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 $109. However, be on the lookout for offers from Cayman Airways 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

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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 julio 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$440Average$556FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$471Average$574FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$485Average$704FlexibilityNo cancel feeOn-time63%

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