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Simpson Bay

Cheap flights from Port of Spain (POS) to Simpson Bay (SXM)

POS — SXM
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Port of Spain Piarco Intl to Simpson Bay Princess Juliana are usually found in April or November, booked 48 days in advance, depart on a Friday or Monday and return on a Monday

Cheap flight deals from Port of Spain to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Port of Spain (POS) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

July

Cheapest in

April

Average price

$563

Good round-trip deal

$513 or less

Good one-way deal

$248 or less
Provider with most accurate pricing for Port of Spain Piarco Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Simpson Bay Princess Juliana flights.
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Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Port of Spain Piarco Intl to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Port of Spain Piarco Intl to Simpson Bay Princess Juliana.
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Compare providers for flights from Port of Spain to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Port of Spain to Simpson Bay in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*2 stars
OneTravelPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Port of Spain-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Port of Spain-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Port of Spain-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Port of Spain-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Port of Spain-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Port of Spain to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Port of Spain with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Port of Spain to Simpson Bay

How far ahead should I book a flight from Port of Spain to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Port of Spain to Simpson Bay. Price data was last updated on September 26, 2025.

The best time to book flights from Port of Spain to Simpson Bay is 48 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Port of Spain to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Port of Spain to Simpson Bay (average of $459). Flying from Port of Spain to Simpson Bay in March is currently the most expensive (average of $651). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from POS to SXM?

Find hourly flight availability from Port of Spain to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

When flying from Port of Spain to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 53% versus a flight in the morning.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated September 29, 2025.
Read reviews from past customers who have flown Caribbean Airlines and Copa Airlines from Port of Spain to Simpson Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.1
Very good
184 reviews

Crew

8.4

Entertainment

6.7

Boarding

8.1

Comfort

7.9

Food

6.8

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Boy,Sep 2025

POS - YYZ

The pasta need to be cut out and some more local dishes need to be serve .
Caribbean Airlines
8.1
Very good
184 reviews
Caribbean Airlines
8.1
Very good
184 reviews

Crew

8.4

Entertainment

6.7

Boarding

8.1

Comfort

7.9

Food

6.8

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Boy,Sep 2025

POS - YYZ

The pasta need to be cut out and some more local dishes need to be serve .
Copa Airlines
7.6
Good
1,542 reviews
Caribbean Airlines
8.1
Very good
184 reviews

Crew

8.4

Entertainment

6.7

Boarding

8.1

Comfort

7.9

Food

6.8

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Boy,Sep 2025

POS - YYZ

The pasta need to be cut out and some more local dishes need to be serve .

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Port of Spain to Simpson Bay flight route?

    This flight path from Port of Spain Piarco Intl to Simpson Bay Princess Juliana was viewed by 31 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • What are the cheapest airlines flying from Port of Spain to Simpson Bay round-trip?

    Flying on Copa Airlines is currently your cheapest option to Simpson Bay, with prices starting at $282. Another option worth looking into is Caribbean Airlines, starting at $458 round trip. Copa Airlines is currently priced 49% below the average price you’ll pay for this route.

  • Can I find deals for flights from Port of Spain to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Port of Spain to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Port of Spain to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Port of Spain to Simpson Bay.

  • Can I find deals for business class flights from Port of Spain to Simpson Bay?

    Yes. Cheapflights offers flight deals from Port of Spain to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Port of Spain to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Port of Spain to Simpson Bay (average of $459). Flying from Port of Spain to Simpson Bay in March is currently the most expensive (average of $651). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top 2 airlines flying from Port of Spain to Simpson Bay

Discover the top 2 airlines that operate flights from Port of Spain to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$282Average$559FlexibilityNo cancel feeOn-time70%
Caribbean AirlinesCheapest$458Average$564FlexibilityNo cancel feeOn-timeN/A

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