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Cayman Islands

$300+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheap 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 March 24, 2026.

This Gotogate deal was found by Cheapflights users on 3/24. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/269:10 am
POS
-
GCM
1 stop27h 25m
Multiple Airlines
Sat 5/28:50 am
GCM
-
POS
1 stop9h 05m
Multiple Airlines
Deal found 3/24$594
This American Airlines deal was found by Cheapflights users on 3/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:47 pm
POS
-
GCM
1 stop44h 13m
American Airlines
Thu 5/142:10 pm
GCM
-
POS
1 stop23h 22m
American Airlines
Deal found 3/22$790
This American Airlines deal was found by Cheapflights users on 3/20. 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.
Mon 5/113:47 pm
POS
-
GCM
1 stop22h 23m
American Airlines
Mon 5/1812:00 pm
GCM
-
POS
1 stop49h 32m
American Airlines
Deal found 3/20$797
This American Airlines deal was found by Cheapflights users on 3/24. 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.
Tue 4/213:47 pm
POS
-
GCM
1 stop22h 23m
American Airlines
Tue 4/2812:00 pm
GCM
-
POS
1 stop25h 32m
American Airlines
Deal found 3/24$816
This American Airlines deal was found by Cheapflights users on 3/24. 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.
Fri 5/153:47 pm
POS
-
GCM
1 stop22h 23m
American Airlines
Thu 5/2112:01 pm
GCM
-
POS
1 stop9h 58m
American Airlines
Deal found 3/24$819
This American Airlines deal was found by Cheapflights users on 3/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/123:47 pm
POS
-
GCM
1 stop44h 13m
American Airlines
Sun 4/192:10 pm
GCM
-
POS
1 stop23h 22m
American Airlines
Deal found 3/22$886
This American Airlines deal was found by Cheapflights users on 3/20. 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 4/73:47 pm
POS
-
GCM
1 stop22h 23m
American Airlines
Tue 4/1412:00 pm
GCM
-
POS
1 stop25h 32m
American Airlines
Deal found 3/20$900

Find 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 March 24, 2026.

Round-trip from

$790
(American Airlines)

One-way from

$300
(SmartFares)
From Trinidad and Tobago to Cayman Islands
Search Deals
One-way flight from Trinidad and Tobago to Cayman Islands
Search Deals

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 March 24, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 5/11

3:47 pm-1:10 pm

1 stop22h 23m

George Town Owen Roberts Intl

Mon 5/18

2:10 pm-2:32 pm

1 stop23h 22m

$810
Quickest round-trip

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 4/21

3:47 pm-11:00 am

1 stop20h 13m

George Town Owen Roberts Intl

Tue 4/28

2:10 pm-2:32 pm

1 stop23h 22m

$816

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 4/7

3:47 pm-1:10 pm

1 stop22h 23m

George Town Owen Roberts Intl

Tue 4/14

12:00 pm-2:32 pm

1 stop25h 32m

$900
Cheapest one-way
Quickest one-way

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 7/28

9:10 am-4:05 pm

1 stop7h 55m

$306

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 3/31

3:10 pm-1:30 pm

1 stop23h 20m

$424

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Wed 7/29

3:16 pm-11:25 am

2 stops21h 09m

$566

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 7/28

3:16 pm-11:25 am

2 stops21h 09m

$616

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 3/30

3:46 am-11:35 am

3 stops56h 49m

$710

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Sorted by cheapest first

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 March 24, 2026.
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
7.1
Good
11,491 reviews

Comfort

7.2

Overall

7.1

Boarding

7.5

Crew

7.9

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.1
Good
11,491 reviews
American Airlines
7.1
Good
11,491 reviews

Comfort

7.2

Overall

7.1

Boarding

7.5

Crew

7.9

Entertainment

6.9

Food

6.4

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 22h 23m. American Airlines provides one of the quickest options available for as low as $810. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$652Average$785FlexibilityNo cancel feeOn-time71%

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