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Simpson Bay

$139+ Cheap flights from Pearson Intl (YYZ) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — SXM
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto Pearson Intl to Simpson Bay Princess Juliana are usually found in September or October, booked 56 days in advance, depart on a Tuesday or Sunday and return on a Saturday

Cheap flight deals from Pearson Intl to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) 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 July 29, 2025.

Round-trip from

$436
(American Airlines)

One-way from

$139
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$477

Good round-trip deal

$437 or less

Good one-way deal

$169 or less
From Toronto Pearson Intl to Simpson Bay Princess Juliana
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One-way flight from Toronto Pearson Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 12% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Toronto Pearson Intl to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Toronto Pearson Intl to Simpson Bay Princess Juliana.
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Find flight deals from Pearson Intl to Simpson Bay

Cheapest flights from Pearson Intl to Simpson Bay
Explore the most affordable flight options available from Pearson Intl to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/237:25 pmYYZ - SXM
1 stop18h 00mAmerican Airlines
Sat 8/301:10 pmSXM - YYZ
1 stop21h 06mAmerican Airlines
Deal found 7/27$436
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:15 pmYYZ - SXM
2 stops43h 14mUnited Airlines
Sat 8/303:55 pmSXM - YYZ
2 stops27h 42mUnited Airlines
Deal found 7/27$442
This Air Transat deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:30 amYYZ - SXM
Nonstop4h 45mAir Transat
Sat 11/291:25 pmSXM - YYZ
Nonstop5h 25mAir Transat
Deal found 7/28$444
This SmartFares deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/78:30 amYYZ - SXM
Nonstop4h 44mWestJet
Sun 9/142:10 pmSXM - YYZ
Nonstop5h 00mWestJet
Deal found 7/28$445
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/296:15 amYYZ - SXM
1 stop7h 35mDelta
Fri 10/33:20 pmSXM - YYZ
1 stop8h 35mDelta
Deal found 7/28$506
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/211:30 pmYYZ - SXM
1 stop24h 30mMultiple Airlines
Sun 9/282:10 pmSXM - YYZ
Nonstop5h 00mMultiple Airlines
Deal found 7/27$511

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pearson Intl to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Simpson Bay that are best for you.

Fly from

Pearson Intl

Fly to

Simpson Bay

Route

Depart

Return

Price

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 8/23

7:25 pm-1:25 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Sat 8/30

1:10 pm-10:16 am

1 stop21h 06m

$436

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 8/21

5:15 pm-12:29 pm

2 stops43h 14m

Simpson Bay Princess Juliana

Sat 8/30

3:55 pm-7:37 pm

2 stops27h 42m

$442

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 9/7

8:30 am-1:14 pm

Nonstop4h 44m

Simpson Bay Princess Juliana

Sun 9/14

2:10 pm-7:10 pm

Nonstop5h 00m

$445

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 9/29

6:15 am-1:50 pm

1 stop7h 35m

Simpson Bay Princess Juliana

Fri 10/3

3:20 pm-11:55 pm

1 stop8h 35m

$506

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 9/21

1:30 pm-2:00 pm

1 stop24h 30m

Simpson Bay Princess Juliana

Sun 9/28

2:10 pm-7:10 pm

Nonstop5h 00m

$511

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 9/6

9:00 am-11:26 am

1 stop26h 26m

$139

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 8/21

9:00 pm-12:29 pm

2 stops39h 29m

$142

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 9/7

8:30 am-1:14 pm

Nonstop4h 44m

$166

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 8/21

3:45 pm-2:31 pm

1 stop22h 46m

$205

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 9/7

9:45 am-10:50 am

1 stop25h 05m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 12 results
1
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Best time to book a flight from Pearson Intl to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Pearson Intl 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 Toronto Pearson Intl Airport to Simpson Bay

How far ahead should I book a flight from Toronto Pearson Intl Airport to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Pearson Intl to Simpson Bay. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Toronto Pearson Intl Airport to Simpson Bay, you should look to book at least 56 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $459). Flying from Toronto Pearson Intl Airport to Simpson Bay in March is currently the most expensive (average of $655). 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 YYZ to SXM?

Find hourly flight availability from Pearson Intl 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 July 29, 2025.

It’s typically best to fly out from Toronto Pearson Intl Airport to Simpson Bay at noon. Doing so could potentially save you 34% on the flight price compared to flying in the morning, which is usually more expensive.

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 July 29, 2025.
Get a feel of what it's like to fly with Caribbean Airlines, Delta, and Copa Airlines from Toronto Pearson Intl Airport to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
Caribbean Airlines
8.1
Very good
166 reviews
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
Delta
8.0
Very good
7,979 reviews
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
Copa Airlines
7.5
Good
1,493 reviews
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
United Airlines
7.4
Good
8,896 reviews
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.
American Airlines
7.2
Good
10,000 reviews
Caribbean Airlines
8.1
Very good
166 reviews

Crew

8.4

Overall

8.1

Food

6.8

Comfort

7.9

Entertainment

6.7

Boarding

8.1

Reviews

1 / 10
6.0
Good

Anonymous,Jul 2025

GEO - POS

The crew was welcoming and helpful. No entertainment no meal only a drink.

Related info for your journey

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

  • What airport do you fly into for flights to Simpson Bay from Toronto Pearson Intl?

    Simpson Bay Princess Juliana (SXM), located 0.5 mi from the city center, is the airport you fly into when you book flights from Toronto Pearson Intl to Simpson Bay. 5 airlines have flights to Princess Juliana from Toronto Pearson Intl on a regular basis. Booking flights from Toronto Pearson Intl to Simpson Bay Princess Juliana should not be difficult; the airport handles an average of 0 inbound flights from Toronto Pearson Intl per day.

  • What are the cheapest airlines flying from Toronto Pearson Intl Airport to Simpson Bay round-trip?

    According to our current data, American Airlines ($436), United Airlines ($442), and WestJet ($445) offers the cheapest pricing from Toronto Pearson Intl Airport to Simpson Bay. American Airlines is 6% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Simpson Bay one-way?

    To fly one-way, consider booking your trip with Copa Airlines, which is currently one of the cheapest options available, starting at $139. United Airlines flights start at $142 while deals on WestJet start at $166 one-way.

  • What are the cheapest flights from Toronto Pearson Intl Airport to Simpson Bay?

    On average you can expect to pay $356 for a flight from Toronto Pearson Intl Airport to Simpson Bay. The cheapest flight overall is $163 while the most popular route, (Toronto Pearson Intl - Simpson Bay Princess Juliana) is currently priced at $353.

  • Can I find deals for flights from Pearson Intl to Simpson Bay that include hotel bookings?

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

  • How can I find direct flights from Pearson Intl to Simpson Bay?

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

  • Can I find deals for business class flights from Pearson Intl to Simpson Bay?

    Yes. Cheapflights offers flight deals from Pearson Intl 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 Toronto Pearson Intl Airport to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $459). Flying from Toronto Pearson Intl Airport to Simpson Bay in March is currently the most expensive (average of $655). 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

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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 5 airlines flying from Pearson Intl to Simpson Bay

Discover the top 5 airlines that operate flights from Pearson Intl 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$279Average$504FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$329Average$542FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$360Average$790FlexibilityNo cancel feeOn-time67%
Air TransatCheapest$365Average$557FlexibilityNo cancel feeOn-time50%
DeltaCheapest$396Average$609FlexibilityNo cancel feeOn-timeN/A

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