$123 Find Cheap Flights from Port of Spain to Caribbean Islands

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 10/8. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Caribbean Islands.
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Flight Deals

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 Cana2 stops$581
Santo Domingo
Santo Domingo1 stop$588
Montego Bay
Montego Bay1 stop$646
Oranjestad
Oranjestad1 stop$560
Nassau
Nassau1 stop$556
Simpson Bay
Simpson Baynonstop$514
Kingston
Kingston1 stop$569
Providenciales
Providenciales1 stop$710
Bridgetown
Bridgetownnonstop$289
George Town
George Town1 stop$592
Willemstad
Willemstadnonstop$257
Castries
Castriesnonstop$299
St. John's
St. John'snonstop$346
Punta Cana
Punta Cana2 stops$581
Santo Domingo
Santo Domingo1 stop$588
Montego Bay
Montego Bay1 stop$646
Oranjestad
Oranjestad1 stop$560
Nassau
Nassau1 stop$556
Simpson Bay
Simpson Baynonstop$514
Kingston
Kingston1 stop$569
Providenciales
Providenciales1 stop$710
Bridgetown
Bridgetownnonstop$289
George Town
George Town1 stop$592
Willemstad
Willemstadnonstop$257
Castries
Castriesnonstop$299
St. John's
St. John'snonstop$346

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

Fri, Nov 7 - Mon, Nov 10
Caribbean Airlines Logo
4:45 pm - 5:50 pmPOS-SVD
1h 05mnonstop
Caribbean Airlines Logo
8:45 pm - 9:50 pmSVD-POS
1h 05mnonstop
$242Caribbean Airlines
Find Deal
Wed, Dec 24 - Sat, Dec 27
Caribbean Airlines Logo
7:05 am - 8:05 amPOS-SVD
1h 00mnonstop
Caribbean Airlines Logo
2:05 pm - 3:05 pmSVD-POS
1h 00mnonstop
$251Caribbean Airlines
Find Deal
Mon, Sep 29 - Sat, Oct 4
Caribbean Airlines Logo
6:55 pm - 8:00 pmPOS-SVD
1h 05mnonstop
Caribbean Airlines Logo
1:30 pm - 2:30 pmSVD-POS
1h 00mnonstop
$267Caribbean Airlines
Find Deal
Sun, Oct 19 - Sun, Oct 26
Multiple Airlines Logo
3:51 am - 1:25 pmPOS-BGI
9h 34m1 stop
Multiple Airlines Logo
5:35 pm - 7:50 pmBGI-POS
2h 15m1 stop
$324Multiple Airlines
Find Deal
Thu, Oct 2 - Tue, Oct 7
Multiple Airlines Logo
3:51 am - 1:25 pmPOS-BGI
9h 34m1 stop
Multiple Airlines Logo
8:55 pm - 9:55 pmBGI-POS
1h 00mnonstop
$330Multiple Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
Copa Airlines Logo
3:51 am - 1:25 pmPOS-BGI
9h 34m1 stop
Copa Airlines Logo
2:42 pm - 1:46 amBGI-POS
11h 04m1 stop
$336Copa Airlines
Find Deal
Tue, Sep 30 - Wed, Oct 8
Copa Airlines Logo
3:51 am - 1:25 pmPOS-BGI
9h 34m1 stop
Copa Airlines Logo
2:42 pm - 1:46 amBGI-POS
11h 04m1 stop
$353Copa Airlines
Find Deal
Thu, Oct 16 - Wed, Oct 22
American Airlines Logo
7:00 am - 8:50 pmPOS-NAS
13h 50m1 stop
American Airlines Logo
2:01 pm - 9:20 pmNAS-POS
7h 19m1 stop
$640American Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
American Airlines Logo
4:30 pm - 2:12 pmPOS-MBJ
46h 42m1 stop
American Airlines Logo
1:40 pm - 3:30 pmMBJ-POS
24h 50m1 stop
$646American Airlines
Find Deal
Mon, Oct 6 - Tue, Oct 14
JetBlue Logo
4:12 pm - 7:51 amPOS-KIN
16h 39m1 stop
JetBlue Logo
8:16 pm - 2:34 pmKIN-POS
17h 18m1 stop
$709JetBlue
Find Deal
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 72 hours 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 72 hours was $307.

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 $439, 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 February, when tickets cost $132 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is $346 and $317 respectively.

What’s the cheapest day of the week to fly from Port of Spain to Caribbean Islands?

The average price of all round-trip flights from Port of Spain to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Port of Spain to Caribbean Islands, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Port of Spain, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Port of Spain to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonMarch
Cheapest flight$123
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 5% increase in price.
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.

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $132 on average. Morning departures are around 30% more expensive than evening flights, 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 $310.

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 $239 one-way - $300 round-trip; St. George's $151 one-way - $295 round-trip; Scarborough $33 one-way - $67 round-trip

Reviews of the top 5 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.
8.1
Caribbean AirlinesOverall score based on 179 reviews
6.8Entertainment
7.9Comfort
8.4Crew
8.1Boarding
6.9Food
Airline reviews

just a child who screamed and threw tantrums the entire flight

8.0 ExcellentAnonymous, Sep 2025YYZ - POS
Read more Caribbean Airlines reviews

just a child who screamed and threw tantrums the entire flight

Excellent experience this was my first time booking with Kayak.

Flight ended up being longer than anticipated because we had to reroute to the Bahamas. So a hour and half flight turned into 5 hours. 0/10.

Flight time. The crew was the rudest, talked down to customers, ignored requests, acted like security guards, used forceful language like must and can't. Everything was on purchase, no entertainment, unless you could use your own phone. Poor customer service.

Checking in, boarding, the food and crew were all excellent. It was my first time traveling on Caribbean Airlines and trust me it’s the only airline I’ll be flying on as of now as long as it’s going my way😁. The service was unbelievably good I don’t regret missing my flight on flair at all cause I wouldn’t have realized how great the service is on Caribbean Airlines

The flight could'nt be better ,the comfort ,the crew and everything was good.i will definitely fly with this sirline again.

I love my entire experience. What I love most, was the friendliness and helpfulness of the staff at check-in and that of the crew on the flight. Their Customer Service was paramount.

The flight crew was extremely hospitable, though there was a lot of turbulence, they made it a good experience. The only negative was the inflight experience for economy class. There wasn’t any, or at least non that I was aware of.

I liked the friendliness of the employees at the airport

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

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Great experience with a crew always thinking in the passenger

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

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.

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

It’s a great flight. Service is good. Staff is awesome.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight was on time and everything went very smoothly.

I was in a wheelchair and went from international to domestic. I was transferred to several different modes of transport and expected to give a tip at each transfer. I was, although, grateful to get to the gate in time for my flight.

Flight was cancelled as I was in line for security. Next available flight got me to my destination 24 hrs later than the first. No refunds offered, just credit toward another flight. I booked with delta, got to my destination only 2 hrs behind my original flight schedule. Won’t be using American again.

Boarding was very smooth and arriving in Miami it was fast getting off the plane

No complaints. Good WiFi, great crew and excellent speedy baggage claim

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

flight cancelled after 2 delays. left us sitting in JFK at 1am. no customer service to assist rebooking.

To not have food or proper snacks on a 5 hour flight was the worst.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

The gate and ground staff were excellent, friendly, went out of their way to acknowledge my Mosaic status. The plane was an older Airbus, so the seats were a little worn. The in flight attendant was not very nice, and seemed to be annoyed to be at work or be on this flight. Flight was fast and we landed early and pilots kept us informed.

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

No priority boarding (travelling with a toddler) and the flight was 4 hours late.

Their online check-in system was offline so the lines at the counter were extremely long. Making our connection was also very unpleasant as there were no priorities for boarding (basically a free-for-all) and since I was travelling with my toddler we had a very hard time. The connecting flight was also 4 hours late.

We were charged an additional $54 usd per passenger to board, not mentioned in the ticket.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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