HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$144+ 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
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pearson Intl to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Toronto Pearson Intl to Simpson Bay Princess Juliana are usually found in September or April, booked 79 days in advance, depart on a Tuesday or Wednesday and return on a Saturday

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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYYZ - SXM
2 stops27h 50mUnited Airlines
Wed 4/293:50 pmSXM - YYZ
1 stop18h 14mUnited Airlines
Deal found 12/10$297
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYYZ - SXM
2 stops27h 50mUnited Airlines
Sat 1/102:40 pmSXM - YYZ
1 stop24h 21mUnited Airlines
Deal found 12/10$299
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYYZ - SXM
2 stops27h 50mUnited Airlines
Wed 4/223:50 pmSXM - YYZ
1 stop22h 29mUnited Airlines
Deal found 12/10$348
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:45 pmYYZ - SXM
1 stop22h 05mUnited Airlines
Wed 4/293:50 pmSXM - YYZ
1 stop18h 14mUnited Airlines
Deal found 12/10$380
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:40 pmYYZ - SXM
2 stops19h 11mUnited Airlines
Sat 1/102:40 pmSXM - YYZ
2 stops22h 08mUnited Airlines
Deal found 12/10$382
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/293:30 pmYYZ - SXM
2 stops21h 20mUnited Airlines
Wed 4/223:50 pmSXM - YYZ
2 stops18h 14mUnited Airlines
Deal found 12/10$417
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYYZ - SXM
2 stops27h 50mUnited Airlines
Tue 1/132:52 pmSXM - YYZ
2 stops33h 54mUnited Airlines
Deal found 12/10$418
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:40 pmYYZ - SXM
1 stop17h 10mUnited Airlines
Wed 4/223:50 pmSXM - YYZ
1 stop8h 04mUnited Airlines
Deal found 12/10$431
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:50 amYYZ - SXM
1 stop8h 07mUnited Airlines
Sun 12/215:00 pmSXM - YYZ
1 stop7h 46mUnited Airlines
Deal found 12/10$447
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:30 amYYZ - SXM
Nonstop4h 45mMultiple Airlines
Mon 12/293:20 pmSXM - YYZ
2 stops17h 43mMultiple Airlines
Deal found 12/10$472

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(United Airlines)

One-way from

$144
(United Airlines)

Popular in

August

Cheapest in

September

Average price

$533

Good round-trip deal

$355 or less

Good one-way deal

$149 or less
Provider with most accurate pricing for Toronto Pearson Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Pearson Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Toronto Pearson Intl to Simpson Bay Princess Juliana
Search Deals
One-way flight from Toronto Pearson Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($8 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 December 2025
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 December 12, 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 4/25

8:55 am-4:49 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Wed 4/29

3:50 pm-9:55 am

2 stops18h 05m

$298

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 1/10

7:40 pm-1:50 pm

1 stop17h 10m

Simpson Bay Princess Juliana

Sun 1/18

4:55 pm-4:02 pm

2 stops24h 07m

$299

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/11

7:30 am-3:51 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Sun 1/18

4:55 pm-4:02 pm

2 stops24h 07m

$299

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 1/24

2:45 pm-3:51 pm

2 stops24h 06m

Simpson Bay Princess Juliana

Thu 1/29

2:52 pm-2:01 pm

2 stops24h 09m

$299

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Tue 1/6

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

Sun 1/18

4:55 pm-9:58 am

2 stops18h 03m

$299

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 1/19

7:40 pm-1:50 pm

2 stops17h 10m

Simpson Bay Princess Juliana

Wed 1/28

2:52 pm-2:14 pm

2 stops24h 22m

$312

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 3/16

9:00 pm-2:51 pm

2 stops17h 51m

$144

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 3/1

7:10 pm-2:05 pm

1 stop17h 55m

$144

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 3/6

6:10 am-3:57 pm

2 stops32h 47m

$145

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 2/28

6:40 pm-1:50 pm

2 stops18h 10m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 14 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 December.
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 December 5, 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 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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $224). 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 December 12, 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.

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 December 12, 2025.
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
7.8
Good
480 reviews

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Overall

7.8

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Transat
7.8
Good
480 reviews
Air Transat
7.8
Good
480 reviews

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Overall

7.8

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
American Airlines
7.2
Good
11,049 reviews
Air Transat
7.8
Good
480 reviews

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Overall

7.8

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
WestJet
7.2
Good
3,195 reviews
Air Transat
7.8
Good
480 reviews

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Overall

7.8

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.
Air Canada
7.1
Good
10,517 reviews
Air Transat
7.8
Good
480 reviews

Boarding

7.9

Entertainment

7.1

Comfort

7.3

Crew

8.4

Overall

7.8

Food

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

YYZ - YUL

Easy, fast onboarding, very friendly staff. Seats were very narrow, OK for me but we were elbow to elbow with both neighbours of small size. The seat width should be indicated at the time of booking to prevent an uncomfortable situation with oversized travellers.

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 1 inbound flight from Toronto Pearson Intl per day.

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

    United Airlines, American 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 45m. 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, Air Canada ($218), WestJet ($284), and American Airlines ($318) offers the cheapest pricing from Toronto Pearson Intl Airport to Simpson Bay. Air Canada is 55% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Consider WestJet (74%), Air Transat (60%) or Air Canada (46%) 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 $376 for a flight from Toronto Pearson Intl Airport to Simpson Bay. The cheapest flight overall is $148 while the most popular route, (Toronto Pearson Intl - Simpson Bay Princess Juliana) is currently priced at $312.

  • 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, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Simpson Bay (average of $224). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$254Average$636FlexibilityNo cancel feeOn-time67%
WestJetCheapest$306Average$536FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$318Average$542FlexibilityNo cancel feeOn-time71%
Air TransatCheapest$405Average$543FlexibilityNo cancel feeOn-time50%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.