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Cheap Flights from Port of Spain to Caribbean Islands

Cheapest return flight prices found by our users on KAYAK in the last 5 days
Bridgetown
Bridgetowndirect£255
Montego Bay
Montego Bay2 stops£635
Kingston
Kingston1 stop£507
Punta Cana
Punta Cana1 stop£431
St. John's
St. John'sdirect£340
Castries
Castriesdirect£321
St. George's
St. George'sdirect£276
Santo Domingo
Santo Domingo1 stop£436
Nassau
Nassau1 stop£489
Simpson Bay
Simpson Bay1 stop£444
Kingstown
Kingstowndirect£238
Basseterre
Basseterre1 stop£553
Oranjestad
Oranjestad1 stop£564
Willemstad
Willemstad1 stop£236
Road Town
Road Town1 stop£508
Bridgetown
Bridgetowndirect£255
Montego Bay
Montego Bay2 stops£635
Kingston
Kingston1 stop£507
Punta Cana
Punta Cana1 stop£431
St. John's
St. John'sdirect£340
Castries
Castriesdirect£321
St. George's
St. George'sdirect£276
Santo Domingo
Santo Domingo1 stop£436
Nassau
Nassau1 stop£489
Simpson Bay
Simpson Bay1 stop£444
Kingstown
Kingstowndirect£238
Basseterre
Basseterre1 stop£553
Oranjestad
Oranjestad1 stop£564
Willemstad
Willemstad1 stop£236
Road Town
Road Town1 stop£508
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?

The cheapest ticket to Caribbean Islands from Port of Spain found in the last 5 days was to Kingston, at £528 return. The most popular route is from Port of Spain (POS) to Kingston (KIN), and the cheapest return airline ticket found on this route in the last 5 days was £528.

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

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when retur flights cost £228 on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is £279.

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

No, with an average price for the route of £375, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Port of Spain to Caribbean Islands is October, when tickets cost £233 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of return tickets is £320 and £308 respectively.

How far in advance should I book a flight from Port of Spain to Caribbean Islands?

To get a below-average price on a flight from Port of Spain to Caribbean Islands, you should book around 4 weeks before departure, which saves you about 18% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know - Cheap tickets from Port of Spain to Caribbean Islands

Low season

February

Cheapest flight

£24
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Port of Spain to Scarborough

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 travellers 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 return 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?

    There is a maximum of 1 direct flight a day that takes off from Port of Spain and lands in Caribbean Islands, with an average flight time of 0h 49m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 3 flights.

Top tips for finding a cheap flight from Port of Spain to Caribbean Islands

  • Looking for a cheap flight from Port of Spain to Caribbean Islands? 25% of our users found tickets from Port of Spain to Caribbean Islands for the following prices or less: Bridgetown £148 one-way - £282 round-trip

Reviews of the top airline flying 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.
7.9
Caribbean AirlinesOverall score based on 231 reviews
8.0Boarding
8.3Crew
6.7Entertainment
6.8Food
7.8Comfort
Airline reviews

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

4.0 OkayAnonymous, Mar 2026
Read more Caribbean Airlines reviews

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports