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Simpson Bay

$129+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 April or September, booked 79 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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.
Sun 3/17:10 pm
YYZ
-
SXM
2 stops18h 09m
American Airlines
Fri 3/65:28 pm
SXM
-
YYZ
2 stops19h 22m
American Airlines
Deal found 1/26$335
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Fri 2/69:00 pm
YYZ
-
SXM
1 stop17h 57m
United Airlines
Mon 2/92:52 pm
SXM
-
YYZ
2 stops24h 09m
United Airlines
Deal found 1/26$337
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/85:22 pm
YYZ
-
SXM
2 stops18h 07m
American Airlines
Mon 3/164:01 pm
SXM
-
YYZ
1 stop18h 17m
American Airlines
Deal found 1/28$340
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:30 pm
YYZ
-
SXM
1 stop21h 27m
United Airlines
Fri 3/64:55 pm
SXM
-
YYZ
1 stop7h 51m
United Airlines
Deal found 1/28$341
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/27:40 pm
YYZ
-
SXM
2 stops17h 10m
United Airlines
Mon 2/92:52 pm
SXM
-
YYZ
2 stops24h 09m
United Airlines
Deal found 1/26$342
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/87:30 am
YYZ
-
SXM
1 stop7h 13m
United Airlines
Wed 4/151:35 pm
SXM
-
YYZ
1 stop8h 48m
United Airlines
Deal found 1/27$344
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/216:40 pm
YYZ
-
SXM
2 stops18h 10m
United Airlines
Sat 2/285:00 pm
SXM
-
YYZ
2 stops19h 48m
United Airlines
Deal found 1/27$346
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 2/87:40 pm
YYZ
-
SXM
2 stops17h 10m
United Airlines
Sun 2/152:52 pm
SXM
-
YYZ
1 stop9h 28m
United Airlines
Deal found 1/27$347
This WestJet deal was found by Cheapflights users on 1/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/279:30 am
YYZ
-
SXM
Nonstop4h 51m
WestJet
Thu 2/54:20 pm
SXM
-
YYZ
Nonstop5h 22m
WestJet
Deal found 1/26$348
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/36:00 am
YYZ
-
SXM
1 stop9h 28m
American Airlines
Tue 2/105:33 pm
SXM
-
YYZ
2 stops18h 35m
American Airlines
Deal found 1/28$353
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:00 am
YYZ
-
SXM
Nonstop4h 50m
WestJet
Thu 5/72:40 pm
SXM
-
YYZ
Nonstop5h 05m
WestJet
Deal found 1/27$356

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(American Airlines)

One-way from

$129
(United Airlines)

Popular in

August

Cheapest in

April

Average price

$448

Good round-trip deal

$503 or less

Good one-way deal

$226 or less
Provider with most accurate pricing for Toronto Pearson Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Toronto Pearson Intl-Simpson Bay Princess Juliana flights.
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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
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Toronto Pearson Intl to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Toronto Pearson Intl to Simpson Bay Princess Juliana.
Search Deals

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 January 29, 2026.
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 2/21

7:40 pm-1:50 pm

1 stop17h 10m

Simpson Bay Princess Juliana

Sat 2/28

5:00 pm-11:46 pm

1 stop7h 46m

$346

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 3/11

7:40 pm-12:50 pm

1 stop17h 10m

Simpson Bay Princess Juliana

Sun 3/15

1:20 pm-11:52 pm

1 stop10h 32m

$346

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 3/23

6:40 pm-12:50 pm

2 stops18h 10m

Simpson Bay Princess Juliana

Tue 3/31

3:50 pm-11:43 am

2 stops19h 53m

$347

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 4/25

8:50 am-4:49 pm

1 stop7h 59m

Simpson Bay Princess Juliana

Wed 4/29

3:50 pm-10:04 am

1 stop18h 14m

$357

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 3/21

3:45 pm-2:57 pm

2 stops23h 12m

Simpson Bay Princess Juliana

Wed 3/25

1:52 pm-3:02 pm

3 stops25h 10m

$363

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 2/27

6:10 am-3:57 pm

2 stops32h 47m

Simpson Bay Princess Juliana

Sat 3/7

2:40 pm-6:45 pm

1 stop29h 05m

$363

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 3/16

6:40 pm-12:50 pm

2 stops18h 10m

Simpson Bay Princess Juliana

Thu 3/19

3:55 pm-9:58 am

2 stops18h 03m

$364

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 2/27

6:10 am-3:57 pm

2 stops32h 47m

Simpson Bay Princess Juliana

Fri 3/6

2:52 pm-2:14 pm

2 stops24h 22m

$364

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 2/28

7:40 pm-1:50 pm

1 stop17h 10m

Simpson Bay Princess Juliana

Fri 3/6

2:52 pm-11:20 pm

1 stop9h 28m

$364

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 3/16

7:40 pm-2:51 pm

2 stops19h 11m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 19 results
1
2

Compare providers for flights from Pearson Intl 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 Pearson Intl to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars

*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 Toronto Pearson Intl Airport-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Pearson Intl Airport-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Pearson Intl Airport-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Pearson Intl Airport-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 Toronto Pearson Intl Airport-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 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 January 23, 2026.

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 79 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, March is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $188). Flying from Toronto Pearson Intl Airport to Simpson Bay in August is currently the most expensive (average of $368). 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 January 29, 2026.

When flying from Toronto Pearson Intl Airport to Simpson Bay, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Simpson Bay?

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 January 29, 2026.
Get a feel of what it's like to fly with Air Transat, American Airlines, and WestJet 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.
Air Transat
7.7
Good
501 reviews

Boarding

7.9

Entertainment

7.0

Comfort

7.3

Food

6.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Transat
7.7
Good
501 reviews
Air Transat
7.7
Good
501 reviews

Boarding

7.9

Entertainment

7.0

Comfort

7.3

Food

6.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
American Airlines
7.2
Good
11,206 reviews
Air Transat
7.7
Good
501 reviews

Boarding

7.9

Entertainment

7.0

Comfort

7.3

Food

6.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
WestJet
7.2
Good
3,253 reviews
Air Transat
7.7
Good
501 reviews

Boarding

7.9

Entertainment

7.0

Comfort

7.3

Food

6.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Canada
7.1
Good
10,666 reviews
Air Transat
7.7
Good
501 reviews

Boarding

7.9

Entertainment

7.0

Comfort

7.3

Food

6.8

Crew

8.4

Overall

7.7

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.

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. 4 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.

  • How long is the flight from Toronto Pearson Intl Airport to Simpson Bay?

    United Airlines can get you from Toronto Pearson Intl Airport to Simpson Bay in just under 17h 10m. Your travel time can differ by up to . Toronto Pearson Intl Airport and Simpson Bay are separated by a distance of 2014 mi.

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

    According to our current data, Air Canada ($254), WestJet ($302), and American Airlines ($318) offers the cheapest pricing from Toronto Pearson Intl Airport to Simpson Bay. Air Canada is 46% 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 WestJet, which is currently one of the cheapest options available, starting at $143. Air Canada flights start at $146 while deals on Air Transat start at $194 one-way.

  • What are the most reliable airlines from Toronto Pearson Intl Airport to Simpson Bay?

    Consider Air Transat (64%), WestJet (60%) or Air Canada (49%) when booking your flight. These represent the most reliable airlines when flying from Toronto Pearson Intl Airport to Simpson Bay.

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

    On average you can expect to pay $392 for a flight from Toronto Pearson Intl Airport to Simpson Bay. The cheapest flight overall is $185 while the most popular route, (Toronto Pearson Intl - Simpson Bay Princess Juliana) is currently priced at $270.

  • 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, March is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $188). Flying from Toronto Pearson Intl Airport to Simpson Bay in August is currently the most expensive (average of $368). 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 4 airlines flying from Pearson Intl to Simpson Bay

Discover the top 4 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$254Average$579FlexibilityNo cancel feeOn-time67%
WestJetCheapest$302Average$535FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$318Average$636FlexibilityNo cancel feeOn-time71%
Air TransatCheapest$355Average$529FlexibilityNo cancel feeOn-time50%

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