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Cayman Islands

$201+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/246:02 amPOS - GCM
2 stops30h 55mAmerican Airlines
Fri 12/261:05 pmGCM - POS
1 stop9h 42mAmerican Airlines
Deal found 12/17$943
This Priceline deal was found by Cheapflights users on 12/17. 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.
Mon 12/223:56 pmPOS - GCM
1 stop23h 39mMultiple Airlines
Wed 12/247:00 amGCM - POS
1 stop10h 55mMultiple Airlines
Deal found 12/17$987
This Priceline deal was found by Cheapflights users on 12/17. 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.
Wed 12/243:55 pmPOS - GCM
1 stop23h 40mMultiple Airlines
Fri 12/267:00 amGCM - POS
1 stop10h 55mMultiple Airlines
Deal found 12/17$1,034
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/224:46 pmPOS - GCM
1 stop28h 32mAmerican Airlines
Wed 12/2412:55 pmGCM - POS
2 stops25h 49mAmerican Airlines
Deal found 12/17$1,077

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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$548
(Booking.com)

One-way from

$201
(SmartFares)
Provider with most accurate pricing for Port of Spain Piarco Intl-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-George Town Owen Roberts Intl flights.
Search Deals
From Trinidad and Tobago to Cayman Islands
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One-way flight from Trinidad and Tobago to Cayman Islands
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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 December 18, 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

Mon 5/11

9:10 am-9:05 pm

1 stop12h 55m

George Town Owen Roberts Intl

Mon 5/18

4:45 pm-6:55 pm

1 stop25h 10m

$548

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 5/11

3:10 pm-10:45 am

1 stop44h 35m

George Town Owen Roberts Intl

Mon 5/18

3:15 pm-2:00 pm

1 stop21h 45m

$691

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 4/21

3:10 pm-10:45 am

1 stop20h 35m

George Town Owen Roberts Intl

Tue 4/28

3:15 pm-2:00 pm

1 stop21h 45m

$716

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/8

3:10 pm-10:45 am

1 stop20h 35m

George Town Owen Roberts Intl

Thu 5/14

1:15 pm-2:00 pm

1 stop23h 45m

$716

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 2/12

6:30 am-8:15 pm

1 stop14h 45m

George Town Owen Roberts Intl

Fri 2/20

1:00 pm-1:18 pm

1 stop23h 18m

$726

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 1/27

9:10 am-4:05 pm

1 stop7h 55m

$201

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sat 1/3

6:02 am-8:18 pm

1 stop15h 16m

$481

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Sat 1/3

10:10 am-11:35 am

3 stops50h 25m

$879

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December 18, 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
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Food

6.5

Comfort

7.2

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
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Food

6.5

Comfort

7.2

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 44h 35m. American Airlines provides one of the quickest options available for as low as $691. 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$757FlexibilityNo cancel feeOn-time71%

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