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Simpson Bay

$134+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 October or September, booked 56 days in advance, depart on a Tuesday or Friday 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 September 11, 2025.

Round-trip from

$368
(American Airlines)

One-way from

$134
(United Airlines)

Popular in

August

Cheapest in

October

Average price

$350

Good round-trip deal

$491 or less

Good one-way deal

$144 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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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($9 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 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 September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/288:30 amYYZ - SXM
Nonstop4h 44mWestJet
Sun 10/52:10 pmSXM - YYZ
Nonstop5h 00mWestJet
Deal found 9/10$372
This United Airlines deal was found by Cheapflights users on 9/9. 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 12/146:52 amYYZ - SXM
1 stop8h 05mUnited Airlines
Mon 12/222:52 pmSXM - YYZ
1 stop9h 28mUnited Airlines
Deal found 9/9$375
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/252:45 pmYYZ - SXM
1 stop24h 12mUnited Airlines
Thu 10/301:52 pmSXM - YYZ
1 stop9h 28mUnited Airlines
Deal found 9/11$376
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:30 amYYZ - SXM
Nonstop4h 45mAir Transat
Sat 11/81:25 pmSXM - YYZ
Nonstop5h 25mAir Transat
Deal found 9/10$378
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/153:52 pmYYZ - SXM
2 stops21h 08mAmerican Airlines
Mon 11/175:24 pmSXM - YYZ
2 stops18h 50mAmerican Airlines
Deal found 9/10$399
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Tue 11/117:40 pmYYZ - SXM
2 stops17h 10mUnited Airlines
Sat 11/152:40 pmSXM - YYZ
1 stop10h 19mUnited Airlines
Deal found 9/9$403
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/53:45 pmYYZ - SXM
2 stops21h 52mAmerican Airlines
Sun 10/122:40 pmSXM - YYZ
1 stop9h 19mAmerican Airlines
Deal found 9/9$405
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Fri 11/146:20 pmYYZ - SXM
2 stops18h 40mAmerican Airlines
Mon 11/175:24 pmSXM - YYZ
2 stops18h 50mAmerican Airlines
Deal found 9/9$406
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 12/297:10 pmYYZ - SXM
1 stop17h 49mAmerican Airlines
Wed 1/75:20 pmSXM - YYZ
2 stops18h 45mAmerican Airlines
Deal found 9/11$420

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 September 11, 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

Sun 12/14

6:52 am-3:57 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 12/22

2:52 pm-11:20 pm

1 stop9h 28m

$375

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 1/2

7:30 am-3:51 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Thu 1/15

2:52 pm-4:02 pm

2 stops26h 10m

$380

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 1/28

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Thu 1/29

4:20 pm-8:43 pm

Nonstop5h 23m

$387

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 1/5

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

Thu 1/15

2:52 pm-4:02 pm

2 stops26h 10m

$391

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 1/26

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Thu 1/29

4:20 pm-8:43 pm

Nonstop5h 23m

$402

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/25

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Wed 2/4

4:20 pm-8:42 pm

Nonstop5h 22m

$402

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 1/26

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Tue 2/3

4:20 pm-8:42 pm

Nonstop5h 22m

$402

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 1/28

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Fri 1/30

4:20 pm-8:43 pm

Nonstop5h 23m

$403

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 1/22

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Fri 1/30

4:20 pm-8:43 pm

Nonstop5h 23m

$403

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 1/28

9:30 am-3:21 pm

Nonstop4h 51m

Simpson Bay Princess Juliana

Mon 2/2

4:20 pm-8:42 pm

Nonstop5h 22m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 19 results
1
2

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 August 29, 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 $652). 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 September 11, 2025.

It’s typically best to fly out from Toronto Pearson Intl Airport to Simpson Bay at noon. Doing so could potentially save you 36% 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 September 11, 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
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
7.7
Good
438 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
3,091 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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 and WestJet can get you from Toronto Pearson Intl Airport to Simpson Bay in just under 4h 51m. Your travel time can differ by up to 3h 14m. Toronto Pearson Intl Airport and Simpson Bay are separated by a distance of 2014 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, WestJet ($325), American Airlines ($329), and Air Canada ($360) offers the cheapest pricing from Toronto Pearson Intl Airport to Simpson Bay. WestJet is 31% 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 $385 for a flight from Toronto Pearson Intl Airport to Simpson Bay. The cheapest flight overall is $144 while the most popular route, (Toronto Pearson Intl - Simpson Bay Princess Juliana) is currently priced at $318.

  • 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 $652). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$325Average$553FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$329Average$542FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$360Average$775FlexibilityNo cancel feeOn-time67%
Air TransatCheapest$389Average$555FlexibilityNo cancel feeOn-time50%
DeltaCheapest$454Average$609FlexibilityNo cancel feeOn-timeN/A

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