$289 Find Cheap Flights from St. John's to Caribbean Islands - Compare and Save

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Cheap Flights from St. John's to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Santo Domingo
Santo Domingononstop$660
Kingston
Kingstonnonstop$636
Simpson Bay
Simpson Bay1 stop$314
Port of Spain
Port of Spain2 stops$600
Bridgetown
Bridgetown1 stop$311
Castries
Castries1 stop$484
Santo Domingo
Santo Domingononstop$660
Kingston
Kingstonnonstop$636
Simpson Bay
Simpson Bay1 stop$314
Port of Spain
Port of Spain2 stops$600
Bridgetown
Bridgetown1 stop$311
Castries
Castries1 stop$484
Booking Insights

KAYAK's insights & trends for St. John's to Caribbean Islands flights

Get data-powered insights and trends into flights from St. John's to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest St. John's to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from St. John's found in the last 5 days was to San Juan, at $366 round-trip. The most popular route is from St. John's (ANU) to Kingston (KIN), and the cheapest round-trip airline ticket found on this route in the last 5 days was $520.

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 morning, when round-trip flights cost $174 on average. Morning departures are around 50% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $344.

Can I save money by flying with a layover from St. John's to Caribbean Islands?

No, with an average price for the route of $619, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from St. John's to Caribbean Islands?

The cheapest month for flights from St. John's to Caribbean Islands is September, when tickets cost $374 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $435 and $434 respectively.

Good to know

Low season

May

Cheapest flight

$289
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from St. John's to Kingston

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from St. John's 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 St. John's to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from St. John's 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 St. John's 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 St. John's 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 St. John's 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 St. John's 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 St. John's and Caribbean Islands per day?

    Each day, there are between 1 and 2 nonstop flights that take off from St. John's and land in Caribbean Islands, with an average flight time of 1h 04m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at Bridgetown. Each week, there are 7 flights. The most frequent day of departure is Friday, when 29% of all weekly flights depart. The fewest flights depart on a Wednesday.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from St. John's to the following destinations at these prices or less: Bridgetown $204 one-way - $360 round-trip; Kingston $447 one-way - $601 round-trip; Simpson Bay $182 one-way - $384 round-trip

Reviews of the top 4 airlines serving from St. John's to Caribbean Islands

 
Need help choosing which airline to fly with from St. John's 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
7.5Food
9.5Crew
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.

Caribbean airline sucks… they have a promotion to bring 60lbs in your suitcase.. meanwhile when you reached your destination (JFK)… your suitcase didn’t show up. They had too much weight so the suitcase was left in Guyana… like WTF????? Stupid promotion.. just like the uneducated people working with the airline. The representative said there is nothing she can do about it… will not use them again.

This flight was great. The plane took off and arrived at the destination an hour early. The crew was pleasant. The food and entertainment options are minimal but adequate for a 1-hour flight. They passed out water and quickly supplied me with a fresh magazine since the previous one had the crossword section filled out.

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.

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

Crew were quite friendly. Food was very poor considering the price of the ticket and the flight time. Could not charge my phone due to USB charger not working..

I wrote to the entertainment and food OK because it was non-applicable All excellent

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.

The crew on bw462 and I believe the leading flight crew Is very rude and her face is not pleasant the way she speaks to pax is not what someone would want to have to deal with on a flight.

I liked the crew and Culture. However, my seat was too narrow and not too comfortable

From the point of checking in I felt as if the agents and crew were like family and friends. The best customer service experience I ever had.

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