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Price, demand and travel trends for Port of Spain to Caribbean Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Port of Spain to Caribbean Islands cheaper or more expensive than last year?

Fares from Port of Spain to Caribbean Islands are about 5% higher than they were in November last year, averaging $373 round-trip.

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

January is typically the cheapest month to fly from Port of Spain to Caribbean Islands, with round-trip fares averaging $345. December and August are usually the most expensive, averaging $483 and $475, respectively.

How do fares from Port of Spain to Caribbean Islands vary by day of the week?

On average, Saturday is the cheapest day to fly from Port of Spain to Caribbean Islands and Wednesday is the most expensive. Looking at the past 12 months of KAYAK data, it's 19% more expensive to fly on a Wednesday compared to Saturday.

What's the best time of day to fly from Port of Spain to Caribbean Islands?

It's cheapest to fly to Caribbean Islands in the afternoon with average prices of $431. The night is the most expensive time to fly, with average prices of $614.

What's the best time to book a flight from Port of Spain to Caribbean Islands?

Book your flights 7 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 16% compared to booking at the last minute (within 2 weeks of departure).

Key details for Port of Spain to Caribbean Islands flights

Low season

January
Beat the crowds with an average 24% drop in travelers.
The most popular month to fly with an average 29% increase in travelers.

Your Port of Spain to Caribbean Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How much should I budget for a flight from Port of Spain to Caribbean Islands?

    Over the past 12 months, round-trip fares from Port of Spain to Caribbean Islands have typically cost between $318 and $626.

  • Which airlines fly nonstop from Port of Spain to Caribbean Islands?

    Based on the flight schedule for the next 3 months, 6 airlines operate nonstop flights from Port of Spain to Caribbean Islands, including:

    • Caribbean Airlines
    • Fly Salone
    • interCaribbean Airways
    • Winair
    • Contour

  • Is it cheaper to fly with a layover from Port of Spain to Caribbean Islands?

    Yes, nonstop flights from Port of Spain to Caribbean Islands average $352 over the past 12 months. Flights with a layover can cost less, cheapest when connecting through Kingstown Argyle Intl (SVD), with average fares of $335.

  • How long is a flight from Port of Spain to Caribbean Islands?

    Nonstop flights from Port of Spain to Caribbean Islands take 47m on average.

  • Which cabin classes are available from Port of Spain to Caribbean Islands?

    On flights from Port of Spain to Caribbean Islands you can book Economy Class, Premium Economy Class or Business Class.

  • What are some popular landmarks around Caribbean Islands?

    Caribbean Islands is home to many popular sights. KAYAK travelers' favorites include:

    • Viejo San Juan
    • Palm Beach
    • Eagle Beach
    • Puerto Rico Convention Center

  • What are the earliest and latest flights from Port of Spain to Caribbean Islands?

    The earliest nonstop flight from Port of Spain to Caribbean Islands departs at 5:45 am and the latest leaves at 11:30 pm. Nonstop flights take about 47m.

Your guide to booking Port of Spain to Caribbean Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 7 weeks before your trip. KAYAK data shows fares in this window are around 16% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Wednesday flights, which are about 19% more expensive.
  • Start your trip in Punta Cana, the most popular destination in Caribbean Islands. From there, it's easy to continue on to other popular spots such as San Juan, Oranjestad and Nassau.

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

 
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.
8.8
WinairOverall score based on 5 reviews
8.4Comfort
8.8Boarding
8.0Food
9.6Crew
8.0Entertainment
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
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.

InterCaribbean seems to always be late. I do not recommend it if you have connecting flights with other airlines. The rates are the same as other regional carriers, but their aircraft are not very comfortable and are often quite hot.

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

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental