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Simpson Bay

$131+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — SXM
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
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 November, booked 58 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

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 octubre 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 11/296:50 amYYZ - SXM
1 stop8h 07mUnited Airlines
sáb. 12/65:00 pmSXM - YYZ
2 stops17h 58mUnited Airlines
Deal found 10/27$344
This United Airlines deal was found by Cheapflights users on 10/27. 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.
vie. 12/129:00 pmYYZ - SXM
1 stop17h 57mUnited Airlines
sáb. 12/202:40 pmSXM - YYZ
1 stop10h 19mUnited Airlines
Deal found 10/27$347
This United Airlines deal was found by Cheapflights users on 10/28. 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.
sáb. 11/13:30 pmYYZ - SXM
1 stop24h 27mUnited Airlines
sáb. 11/85:00 pmSXM - YYZ
1 stop7h 46mUnited Airlines
Deal found 10/28$359
This United Airlines deal was found by Cheapflights users on 10/26. 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.
vie. 11/145:30 pmYYZ - SXM
1 stop21h 27mUnited Airlines
mar. 11/182:52 pmSXM - YYZ
1 stop9h 28mUnited Airlines
Deal found 10/26$369
This United Airlines deal was found by Cheapflights users on 10/27. 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.
mar. 10/287:40 pmYYZ - SXM
2 stops17h 10mUnited Airlines
dom. 11/23:00 pmSXM - YYZ
1 stop31h 21mUnited Airlines
Deal found 10/27$393
This WestJet deal was found by Cheapflights users on 10/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/249:30 amYYZ - SXM
Nonstop4h 51mWestJet
mar. 12/304:20 pmSXM - YYZ
Nonstop5h 23mWestJet
Deal found 10/27$395
This United Airlines deal was found by Cheapflights users on 10/28. 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.
sáb. 11/86:10 amYYZ - SXM
2 stops32h 47mUnited Airlines
sáb. 11/155:00 pmSXM - YYZ
2 stops17h 58mUnited Airlines
Deal found 10/28$398
This American Airlines deal was found by Cheapflights users on 10/26. 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.
lun. 11/36:00 amYYZ - SXM
1 stop9h 22mAmerican Airlines
mié. 11/52:51 pmSXM - YYZ
2 stops20h 22mAmerican Airlines
Deal found 10/26$418

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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$339
(United Airlines)

One-way from

$131
(United Airlines)

Popular in

August

Cheapest in

September

Average price

$455

Good round-trip deal

$415 or less

Good one-way deal

$302 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
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 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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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 octubre 28, 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

sáb. 11/29

6:50 am-3:57 pm

1 stop8h 07m

Simpson Bay Princess Juliana

sáb. 12/6

5:00 pm-9:58 am

2 stops17h 58m

$344

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

vie. 12/12

9:00 pm-3:57 pm

1 stop17h 57m

Simpson Bay Princess Juliana

sáb. 12/20

2:40 pm-11:59 pm

1 stop10h 19m

$347

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

sáb. 1/31

7:40 pm-1:50 pm

1 stop17h 10m

Simpson Bay Princess Juliana

sáb. 2/7

2:40 pm-11:54 pm

1 stop10h 14m

$350

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

dom. 1/18

7:30 am-3:51 pm

1 stop7h 21m

Simpson Bay Princess Juliana

mié. 1/28

2:52 pm-9:58 am

2 stops20h 06m

$358

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

dom. 2/1

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

mar. 2/3

2:52 pm-9:58 am

2 stops20h 06m

$358

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

vie. 1/30

9:00 pm-3:57 pm

1 stop17h 57m

Simpson Bay Princess Juliana

mar. 2/3

2:52 pm-9:58 am

2 stops20h 06m

$358

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

lun. 1/26

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

dom. 2/1

4:55 pm-2:14 pm

1 stop22h 19m

$358

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

dom. 2/1

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

jue. 2/5

2:52 pm-2:01 pm

2 stops24h 09m

$358

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

mié. 11/12

10:00 am-1:50 pm

2 stops26h 50m

$131

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

vie. 12/12

5:30 pm-3:57 pm

1 stop21h 27m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Trip.comPrice Accuracy2 starsTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto Pearson Intl Airport-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 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 58 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, November is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $159). 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 octubre 28, 2025.

It’s typically best to fly out from Toronto Pearson Intl Airport to Simpson Bay in the afternoon. Doing so could potentially save you 32% 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 octubre 28, 2025.
Get a feel of what it's like to fly with Delta, Air Transat, and American 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.
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta
Air Transat
7.8
Good
469 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta
WestJet
7.2
Good
3,148 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta
Air Canada
7.1
Good
10,371 reviews
Delta
7.9
Good
7,994 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MAD - JFK

The delta and planes are getting old. Tv screen would blink off and on every time the person in front of me moved Storage area torn and drooping. Time for and update Delta

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.

  • 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 8h 07m. 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 ($303), American Airlines ($318), and WestJet ($324) offers the cheapest pricing from Toronto Pearson Intl Airport to Simpson Bay. Air Canada is 38% cheaper than the average price of flights available within the next 90 days to this destination.

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

    On average you can expect to pay $409 for a flight from Toronto Pearson Intl Airport to Simpson Bay. The cheapest flight overall is $205 while the most popular route, (Toronto Pearson Intl - Simpson Bay Princess Juliana) is currently priced at $339.

  • 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, November is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $159). 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 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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$303Average$638FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$318Average$542FlexibilityNo cancel feeOn-time71%
WestJetCheapest$324Average$553FlexibilityNo cancel feeOn-time60%
Air TransatCheapest$389Average$547FlexibilityNo cancel feeOn-time50%
DeltaCheapest$503Average$609FlexibilityNo cancel feeOn-timeN/A

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