$352+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Sep 13 — Sep 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Trinidad and Tobago to Cayman Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Trinidad and Tobago to Cayman Islands
Cheapest
Best
Last-minute
One-way
Cheapest flights from Trinidad and Tobago to Cayman IslandsExplore 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 August 14, 2026.
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 August 14, 2026.
This Priceline deal was found by Cheapflights users on 8/10. 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.
Fri 12/49:10 am -
1 stop13h 05m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$575
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Thu 12/36:00 am -
1 stop9h 45m
Mon 12/1412:55 pm -
1 stop9h 40m
Deal found 8/10![American Airlines logo]()
$671
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/26:00 am -
1 stop14h 58m
Thu 12/108:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$677
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/26:00 am -
1 stop9h 45m
Wed 12/98:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$683
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/14:42 pm -
1 stop23h 03m
Thu 12/1012:55 pm -
1 stop9h 40m
Deal found 8/10![American Airlines logo]()
$724
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/14:42 pm -
1 stop20h 13m
Wed 12/98:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$729
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:10 am -
1 stop13h 05m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$737
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/69:10 am -
1 stop27h 25m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$738
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:10 am -
1 stop27h 25m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$744
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:10 am -
1 stop13h 05m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$754
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/26:00 am -
1 stop9h 45m
Fri 12/118:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$761
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/26:00 am -
1 stop14h 58m
Sun 12/138:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$767
Best flights from Trinidad and Tobago to Cayman IslandsDiscover carefully curated flight deals from Trinidad and Tobago to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
Discover carefully curated flight deals from Trinidad and Tobago to Cayman Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2026.
This Priceline deal was found by Cheapflights users on 8/10. 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.
Fri 12/49:10 am -
1 stop13h 05m
Fri 12/117:00 am -
1 stop10h 55m
Deal found 8/10![Multiple Airlines logo]()
$575
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Thu 12/36:00 am -
1 stop9h 45m
Thu 12/1012:55 pm -
1 stop9h 40m
Deal found 8/10![American Airlines logo]()
$671
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/14:42 pm -
1 stop23h 03m
Tue 12/88:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$724
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/56:00 am -
1 stop14h 58m
Sun 12/138:15 am -
1 stop14h 20m
Deal found 8/10![American Airlines logo]()
$761
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Thu 12/36:00 am -
2 stops30h 23m
Wed 12/912:55 pm -
1 stop9h 40m
Deal found 8/10![American Airlines logo]()
$946
This American Airlines deal was found by Cheapflights users on 8/10. 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 12/66:00 am -
2 stops30h 23m
Tue 12/812:55 pm -
1 stop9h 40m
Deal found 8/10![American Airlines logo]()
$952
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:19 pm -
2 stops45h 06m
Thu 8/277:00 am -
3 stops14h 15m
Deal found 8/14![Multiple Airlines logo]()
$2,095
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:19 pm -
2 stops45h 06m
Fri 8/287:00 am -
1 stop10h 55m
Deal found 8/14![Multiple Airlines logo]()
$2,164
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/243:15 pm -
1 stop22h 55m
Sat 8/292:10 pm -
1 stop8h 08m
Deal found 8/14![American Airlines logo]()
$2,012
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/247:00 am -
1 stop29h 00m
Thu 8/2712:00 pm -
1 stop10h 18m
Deal found 8/14![American Airlines logo]()
$2,033
Last-minute flights from Trinidad and Tobago to Cayman IslandsDiscover last-minute flight deals from Trinidad and Tobago to Cayman Islands. Data last updated August 14, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Cayman Islands. Data last updated August 14, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/193:15 pm -
1 stop22h 55m
Thu 11/1912:59 pm -
1 stop25h 34m
Deal found 8/11![American Airlines logo]()
$846
This Mytrip deal was found by Cheapflights users on 8/11. 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.
Wed 8/1912:25 pm -
2 stops9h 35m
Thu 11/197:00 am -
3 stops14h 15m
Deal found 8/11![Multiple Airlines logo]()
$1,752
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 8/227:00 am -
1 stop29h 00m
Sat 8/292:10 pm -
1 stop8h 08m
Deal found 8/14![American Airlines logo]()
$2,085
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 8/227:00 am -
1 stop29h 00m
Thu 8/2712:00 pm -
1 stop10h 18m
Deal found 8/14![American Airlines logo]()
$2,106
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/237:00 am -
1 stop29h 00m
Fri 8/2812:00 pm -
1 stop10h 18m
Deal found 8/14![American Airlines logo]()
$1,632
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/237:00 am -
1 stop29h 00m
Sat 8/292:10 pm -
1 stop8h 08m
Deal found 8/14![American Airlines logo]()
$2,090
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/243:15 pm -
1 stop22h 55m
Sat 8/292:10 pm -
1 stop8h 08m
Deal found 8/14![American Airlines logo]()
$2,012
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/247:00 am -
1 stop29h 00m
Thu 8/2712:00 pm -
1 stop10h 18m
Deal found 8/14![American Airlines logo]()
$2,033
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/243:15 pm -
1 stop22h 55m
Fri 8/282:10 pm -
1 stop8h 08m
Deal found 8/14![American Airlines logo]()
$2,094
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:19 pm -
2 stops45h 06m
Thu 8/277:00 am -
3 stops14h 15m
Deal found 8/14![Multiple Airlines logo]()
$2,095
One-way flights from Trinidad and Tobago to Cayman IslandsSearch for one-way flight options from Trinidad and Tobago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
Search for one-way flight options from Trinidad and Tobago to Cayman Islands. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/313:15 pm -
1 stop20h 45m
Deal found 8/14![American Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:19 pm -
2 stops26h 46m
Deal found 8/14![Multiple Airlines logo]()
$447
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 August 14, 2026.
Round-trip from | $575 (Priceline) |
|---|---|
One-way from | $352 (American Airlines) |
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 August 14, 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
Cheapest round-trip
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Fri 12/4
9:10 am-9:15 pm
1 stop13h 05m
George Town Owen Roberts Intl
Fri 12/11
7:00 am-6:55 pm
1 stop10h 55m
$575
Quickest round-trip
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Thu 12/3
6:00 am-2:45 pm
1 stop9h 45m
George Town Owen Roberts Intl
Thu 12/10
12:55 pm-11:35 pm
1 stop9h 40m
$671
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Tue 12/1
4:42 pm-2:45 pm
1 stop23h 03m
George Town Owen Roberts Intl
Tue 12/8
8:15 am-11:35 pm
1 stop14h 20m
$724
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Sat 12/5
6:00 am-7:58 pm
1 stop14h 58m
George Town Owen Roberts Intl
Sun 12/13
8:15 am-11:35 pm
1 stop14h 20m
$761
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Thu 12/3
6:00 am-11:23 am
2 stops30h 23m
George Town Owen Roberts Intl
Wed 12/9
12:55 pm-11:35 pm
1 stop9h 40m
$946
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Sun 12/6
6:00 am-11:23 am
2 stops30h 23m
George Town Owen Roberts Intl
Tue 12/8
12:55 pm-11:35 pm
1 stop9h 40m
$952
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Mon 8/24
3:15 pm-1:10 pm
1 stop22h 55m
George Town Owen Roberts Intl
Sat 8/29
2:10 pm-11:18 pm
1 stop8h 08m
$2,012
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Mon 8/24
7:00 am-11:00 am
1 stop29h 00m
George Town Owen Roberts Intl
Thu 8/27
12:00 pm-11:18 pm
1 stop10h 18m
$2,033
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Mon 8/24
2:19 pm-10:25 am
2 stops45h 06m
George Town Owen Roberts Intl
Thu 8/27
7:00 am-10:15 pm
3 stops14h 15m
$2,095
Port of SpainGeorge Town
POS Port of Spain Piarco Intl - GCM George Town Owen Roberts Intl
POSGCM
Port of Spain Piarco Intl
Mon 8/24
2:19 pm-10:25 am
2 stops45h 06m
George Town Owen Roberts Intl
Fri 8/28
7:00 am-6:55 pm
1 stop10h 55m
$2,164
Showing 1-10 of 12 resultsSorted 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.
POS-GCM
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
TT0-KY0
POS-GCM
No data available for this route at this time. Please check back soon.
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top regions