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Cayman Islands

$446+ Cheap flights from Trinidad and Tobago 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 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Cayman Islands

Keep the following information in mind while searching for Trinidad and Tobago to Cayman Islands flight deals. Data was last updated September 16, 2025.

Round-trip from

$592
(Booking.com)

One-way from

$446
(Kiwi.com)
From Trinidad and Tobago to Cayman Islands
Search Deals
One-way flight from Trinidad and Tobago to Cayman Islands
Search Deals

Find flight deals from Trinidad and Tobago to Cayman Islands

Cheapest flights from Trinidad and Tobago to Cayman Islands
Explore the most affordable flight options available from Trinidad and Tobago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/319:10 amPOS - GCM
1 stop13h 05mMultiple Airlines
Wed 11/55:10 pmGCM - POS
2 stops19h 45mMultiple Airlines
Deal found 9/15$700
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.
Fri 11/77:19 amPOS - GCM
1 stop14h 09mAmerican Airlines
Fri 11/149:00 amGCM - POS
1 stop13h 39mAmerican Airlines
Deal found 9/13$713
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 11/97:19 amPOS - GCM
1 stop14h 09mAmerican Airlines
Sun 11/309:00 amGCM - POS
1 stop13h 38mAmerican Airlines
Deal found 9/14$893
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/62:15 amPOS - GCM
1 stop11h 10mMultiple Airlines
Fri 11/147:00 amGCM - POS
2 stops17h 10mMultiple Airlines
Deal found 9/15$1,087

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago 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 16, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to the Cayman Islands that are best for you.

Fly from

Trinidad and Tobago

Fly to

Cayman Islands

Route

Depart

Return

Price

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 11/7

7:19 am-8:28 pm

1 stop14h 09m

George Town Owen Roberts Intl

Fri 11/14

9:00 am-11:39 pm

1 stop13h 39m

$713

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sun 11/9

7:19 am-8:28 pm

1 stop14h 09m

George Town Owen Roberts Intl

Sun 11/30

9:00 am-11:38 pm

1 stop13h 38m

$893

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 10/31

7:55 am-9:15 pm

3 stops14h 20m

George Town Owen Roberts Intl

Wed 11/5

5:10 pm-1:55 pm

2 stops19h 45m

$959

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sat 11/29

1:55 am-1:44 pm

1 stop12h 49m

$499

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sat 11/15

7:19 am-8:28 pm

1 stop14h 09m

$691

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sun 11/30

7:19 am-2:46 pm

1 stop8h 27m

$866

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 11/14

3:48 am-11:35 am

2 stops32h 47m

$1,082

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Best time to book a flight from Trinidad and Tobago to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Trinidad and Tobago 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 Trinidad and Tobago to the Cayman Islands
No data available for this route at this time. Please check back soon.

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 September 16, 2025.
Read reviews from past customers who have flown American Airlines from Trinidad and Tobago to the Cayman Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago 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 Trinidad and Tobago to Cayman Islands?

    A quick flight from Trinidad and Tobago to Cayman Islands can take about 14h 09m. American Airlines provides one of the quickest options available for as low as $713. Airlines will cover a distance of 1463 mi.

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

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

  • How can I find direct flights from Trinidad and Tobago to Cayman Islands?

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

  • Can I find deals for business class flights from Trinidad and Tobago to Cayman Islands?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago 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 Trinidad and Tobago to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Trinidad and Tobago to Cayman Islands (average of $467). Flying from Trinidad and Tobago 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 Trinidad and Tobago to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Trinidad and Tobago to Cayman Islands

Discover the top airline that operate flights from Trinidad and Tobago 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$767FlexibilityNo cancel feeOn-time71%

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