$122 Find Cheap Flights from Simpson Bay to Caribbean Islands - Compare and Save

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Cheap Flights from Simpson Bay to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Gustavia
0h 15mNonstop
from $206per person
Santo Domingo
1h 30mNonstop
from $209per person
San Juan
1h 20mNonstop
from $286per person
Roseau
1h 00mNonstop
from $357per person
Willemstad
1h 45mNonstop
from $457per person
George Town
21h 25m3 stops
from $649per person
Kingston
2h 30mNonstop
from $679per person
Booking Insights

KAYAK's insights & trends for Simpson Bay to Caribbean Islands flights

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

What is the cheapest Simpson Bay to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Simpson Bay found in the last 5 days was to Santo Domingo, at $246 round-trip. The most popular route is from Simpson Bay (SXM) to Santo Domingo (SDQ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $246.

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 $336 on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $363.

Can I save money by flying with a layover from Simpson Bay to Caribbean Islands?

No, with an average price for the route of $593, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Simpson Bay to Caribbean Islands?

The cheapest month for flights from Simpson Bay to Caribbean Islands is June, when tickets cost $357 (return) on average. On the other hand, the most expensive months are October and May, when the average cost of round-trip tickets is $412 and $403 respectively.

What’s the cheapest day of the week to fly from Simpson Bay to Caribbean Islands?

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

Good to know

Low season

January

Cheapest flight

$122
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Simpson Bay to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Simpson Bay 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 Simpson Bay to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Simpson Bay 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 Simpson Bay 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 Simpson Bay 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 Simpson Bay 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 Simpson Bay to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Simpson Bay to the following destinations at these prices or less: Willemstad $342 one-way - $543 round-trip; Port of Spain $507 one-way - $996 round-trip; Santo Domingo $187 one-way - $356 round-trip

Reviews of the top 4 airlines serving from Simpson Bay to Caribbean Islands

 
Need help choosing which airline to fly with from Simpson Bay 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
8.5Boarding
7.5Entertainment
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
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.

Boarding the flight was smooth and the flight was not full so i had an extra seat essentially

Little space for luggage and the flight was delayed by an hour.

Excellent experience this was my first time booking with Kayak.

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

STEWARDESSES WERE AWESOME! The food could be a bit better. Rice was SOGGY with gravy and the chicken was RUBBERY.

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

We booked Caribbean Plus and Business Class.. The problem was that in Toronto the staff we would collect our bags in POS, but we had to pick up our luggage in GEO, do immigration, and customers, and go from one terminal to the other with all our suitcases and 2 kids.. Not nice and not cool. Wont do that layover in GEO again

Flight was good, staff and crew was informative. Should have some sort and of entertainment during the flight given the price to fly.🙏

Wearing masks should be enforced in the lounge. There were a few patrons who just weren't wearing them even though it's mandatory in public places in Trinidad and Tobago. Other than that, it was a great experience.

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

More options for your flight to Caribbean Islands

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