$138 Find Cheap Flights from Port of Spain to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Port of Spain to Caribbean Islands departing on 9/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Port of Spain to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$584
Santo Domingo
Santo Domingo1 stop$725
Montego Bay
Montego Bay1 stop$910
Oranjestad
Oranjestad2 stops$647
Nassau
Nassau1 stop$539
Kingston
Kingston1 stop$619
Simpson Bay
Simpson Baynonstop$508
Providenciales
Providenciales1 stop$869
Bridgetown
Bridgetownnonstop$245
George Town
George Town1 stop$561
Willemstad
Willemstad1 stop$316
Castries
Castriesnonstop$388
St. John's
St. John'snonstop$428
Punta Cana
Punta Cana1 stop$584
Santo Domingo
Santo Domingo1 stop$725
Montego Bay
Montego Bay1 stop$910
Oranjestad
Oranjestad2 stops$647
Nassau
Nassau1 stop$539
Kingston
Kingston1 stop$619
Simpson Bay
Simpson Baynonstop$508
Providenciales
Providenciales1 stop$869
Bridgetown
Bridgetownnonstop$245
George Town
George Town1 stop$561
Willemstad
Willemstad1 stop$316
Castries
Castriesnonstop$388
St. John's
St. John'snonstop$428

Book Cheap Port of Spain to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Port of Spain to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Port of Spain to Caribbean Islands

Mon, Sep 21 - Sun, Oct 4
interCaribbean Airways Logo
9:00 am - 9:55 am
POS
-
BGI
0h 55mnonstop
interCaribbean Airways Logo
6:45 pm - 7:40 pm
BGI
-
POS
0h 55mnonstop
$245interCaribbean Airways
Mon, Sep 21 - Sun, Oct 4
interCaribbean Airways Logo
9:00 am - 9:55 am
POS
-
BGI
0h 55mnonstop
interCaribbean Airways Logo
6:45 pm - 7:40 pm
BGI
-
POS
0h 55mnonstop
$258interCaribbean Airways
Sat, Aug 29 - Mon, Aug 31
Caribbean Airlines Logo
12:50 pm - 1:30 pm
POS
-
GND
0h 40mnonstop
Caribbean Airlines Logo
8:55 am - 9:35 am
GND
-
POS
0h 40mnonstop
$325Caribbean Airlines
Wed, Sep 23 - Sun, Sep 27
Multiple Airlines Logo
2:05 pm - 3:05 pm
POS
-
BGI
1h 00mnonstop
Multiple Airlines Logo
9:40 am - 4:10 pm
BGI
-
POS
6h 30m
3 stops
$326Multiple Airlines
Mon, Aug 31 - Sun, Sep 6
Multiple Airlines Logo
11:20 am - 12:20 pm
POS
-
BGI
1h 00mnonstop
Multiple Airlines Logo
6:45 pm - 7:40 pm
BGI
-
POS
0h 55mnonstop
$327Multiple Airlines
Mon, Sep 21 - Sun, Oct 4
Caribbean Airlines Logo
11:05 am - 12:05 pm
POS
-
BGI
1h 00mnonstop
Caribbean Airlines Logo
4:00 pm - 6:20 pm
BGI
-
POS
2h 20m
1 stop
$328Caribbean Airlines
Sat, Aug 8 - Wed, Aug 26
Copa Airlines Logo
3:50 am - 5:36 pm
POS
-
PUJ
13h 46m
1 stop
Copa Airlines Logo
12:07 pm - 1:17 pm
PUJ
-
POS
25h 10m
1 stop
$584Copa Airlines
Thu, Aug 20 - Fri, Aug 28
Copa Airlines Logo
3:50 am - 5:36 pm
POS
-
PUJ
13h 46m
1 stop
Copa Airlines Logo
1:59 pm - 1:17 pm
PUJ
-
POS
23h 18m
1 stop
$595Copa Airlines
Sat, Aug 8 - Sat, Aug 15
American Airlines Logo
7:00 am - 11:00 am
POS
-
GCM
29h 00m
1 stop
American Airlines Logo
11:55 am - 11:18 pm
GCM
-
POS
10h 23m
1 stop
$715American Airlines
Wed, Sep 23 - Wed, Oct 7
American Airlines Logo
3:06 pm - 11:00 am
POS
-
GCM
20h 54m
1 stop
American Airlines Logo
8:00 am - 2:07 pm
GCM
-
POS
53h 07m
1 stop
$742American Airlines
Booking Insights

KAYAK's insights & trends for Port of Spain to Caribbean Islands flights

Get data-powered insights and trends into flights from Port of Spain to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Port of Spain to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Port of Spain found in the last 5 days was to San Juan, at $303 round-trip. The most popular route is from Port of Spain (POS) to Willemstad (CUR), and the cheapest round-trip airline ticket found on this route in the last 5 days was $317.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Port of Spain to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $224 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $302.

Can I save money by flying with a layover from Port of Spain to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $492, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Port of Spain to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Port of Spain to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Port of Spain to Caribbean Islands is October, when tickets cost $313 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $463 and $413 respectively.

Good to know

Low season

January

Cheapest flight

$138
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Port of Spain to Bridgetown

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Port of Spain to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Port of Spain to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Port of Spain to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Port of Spain to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Port of Spain to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Port of Spain to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Port of Spain to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Port of Spain to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Port of Spain and Caribbean Islands per day?

    Each day, there are between 1 and 2 nonstop flights that take off from Port of Spain and land in Caribbean Islands, with an average flight time of 0h 50m. The most common departure time is 7:00 am and most flights take off in the morning, while the most flights land at Scarborough. Each week, there are 5 flights. The most frequent day of departure is Friday, when 40% of all weekly flights depart. The fewest flights depart on a Monday.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Port of Spain to the following destinations at these prices or less: Bridgetown $237 one-way - $325 round-trip; Scarborough $30 one-way - $61 round-trip

Reviews of the top 4 airlines serving from Port of Spain to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Port of Spain to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Port of Spain to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.5
WinairOverall score based on 4 reviews
7.5Entertainment
8.5Boarding
8.0Comfort
9.5Crew
7.5Food
Airline reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

6.0 GoodAnonymous, May 2026
SBH - SXM
Read more Winair reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

Delayed for 3 hours- little to no communication about this and staff moves in slow motion

Nothing, they could have made some accommodation for an awful experience. Me and my family were not informed properly we we separated. They took me off the original flight i booked. I booked our flight at one price and called me and told me they were not honoring my rate and they charged me double of what I paid. Me and my family don’t want to ever use your services again.

Better movie and tv selections. Also, the overnight flight to Trinidad from Toronto, the staff were not very attentive. I did not see them for at least half the fight. They were behind their curtain a lot of the time, and they did not check on us before landing to make sure all landing requirements were met.

I liked the extra leg room in Caribbean plus. Worth the extra money. The food could have been more balanced, there was no salad or veggies

The Flight itself was smooth and uneventful. The crew was polite and caring. I used the Lounge in Piarco and the service was STELLAR

Music would have been great and information about the flight. Meaning how high and the weather conditions.

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Checking in was seamless Flight left on time Flight arrived 45 minutes ahead of time, Overall, it was a good experience

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

Seats were awful. Media should have been included for such a long flight.

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Very happy with my flight. I would definitely recommend it.

Very good flight and crew Food was a surprise on a short flight

Seemed roomier than most US domestic airlines and they served food.

Crew were all excellent. Wheel chair access for my parents was very good, although it took some time. Plane was ok but entertainment system did not work. NO WIFI on plane so could not get other things done while flying or listen to my Apple Music on my iPhone.

other than a slight delay in takeoff from Panama , the flights were excellent ..... we will continue to use Copa whenever possible for flights to and from Central and South America ....

I was fortunate enough to have an entire row to myself and that was the highlight. Unfortunately, the flight was really turbulent which had no impact on how effective the crew was. However, I am disabled and should have boarded the flight first, but that wasn't the case. They also decided to take my bag at the gate because I had one too many and upon my picking it up at JFK it along with my rollator had been damaged. I am a vegan so the didn't have a proper meal for me and I was unable to view the entertainment because I didn't receive a set of headphones and if I needed to supply my own I wasn't made aware of that either. The crew was great, but overall everything was pretty lackluster.

Flew St Vincent to Barbados on an ATR-40 (?), seating about 60 passengers. Pretty tight in there. Flt. attendant was very friendly. Short flight - up & down in 40 minutes.

No food, no entertainment - half-hour flight (up & down) Smallest plane I’ve ever been on - maybe 60 passenger capacity?

I've had bad flights with InterCaribbean before (cancellations, no gate agents, etc.), but this one went perfectly smoothly!

Long delay. No AC on the flight from Barbados to St. Lucia.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports