Which airlines fly to Simpson Bay?

WestJet, Air Canada and Air Transat are the top three most popular airlines that fly to Simpson Bay from Toronto according to our data. WestJet is the first choice among our users, with 70% of people opting to fly with this airline when travelling to Simpson Bay. Keep in mind that there are 7 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Toronto to Simpson Bay?

Flights via Miami (MIA) offer the lowest average round-trip price of C$ 461.

What is the cheapest airline that flies from Toronto to Simpson Bay Princess Juliana?

United Airlines, American Airlines, and Air Canada are the most popular carriers operating from Toronto to Simpson Bay Princess Juliana

Which layover airport has the shortest connection time from Toronto to Simpson Bay?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 11m.

Which layover airport has the shortest travel time from Toronto to Simpson Bay?

Flights connecting via Washington, D.C. (IAD) have the shortest average one-way travel time: 6h 36m.

Which airport is the most popular layover for flights between Toronto and Simpson Bay?

Miami (MIA) was the most common stop: 40% of momondo users choosing one-stop flights on this route connected there.

When did momondo last update prices for flights from Toronto to Simpson Bay Princess Juliana Airport?

Prices for flights from Toronto to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Toronto to Simpson Bay Princess Juliana Airport?

As of October 2025, there are 7 operators available to choose from for flights from Toronto to Simpson Bay Princess Juliana Airport.

How old do you have to be to fly from Toronto to Simpson Bay Princess Juliana Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 184 Cheap Flights from Toronto to Simpson Bay in 2025/26

1 adult

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Find the cheapest flights from Toronto to Simpson Bay

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Cheap round-trip flights

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7:40 p.m. - 3:57 p.m.YYZ-SXM

20h 17m2 stops

3:00 p.m. - 11:59 p.m.SXM-YYZ

9h 59m1 stop

C$ 466United Airlines

Find Deal

Sat, 1 Nov - Sun, 9 Nov

6:00 a.m. - 4:28 p.m.YYZ-SXM

9h 28m1 stop

3:50 p.m. - 10:19 a.m.SXM-YYZ

19h 29m1 stop

C$ 470American Airlines

Find Deal

Mon, 19 Jan - Sun, 25 Jan

9:30 a.m. - 3:21 p.m.YYZ-SXM

4h 51mdirect

4:20 p.m. - 8:43 p.m.SXM-YYZ

5h 23mdirect

C$ 476WestJet

Find Deal

Mon, 15 Dec - Thu, 18 Dec

9:30 a.m. - 3:21 p.m.YYZ-SXM

4h 51mdirect

4:20 p.m. - 8:43 p.m.SXM-YYZ

5h 23mdirect

C$ 505WestJet

Find Deal

Tue, 16 Dec - Fri, 19 Dec

5:00 p.m. - 11:55 a.m.YYZ-SXM

17h 55m1 stop

1:25 p.m. - 5:50 p.m.SXM-YYZ

5h 25mdirect

C$ 531Air Transat

Find Deal

Tue, 3 Feb - Tue, 17 Feb

8:15 a.m. - 11:55 a.m.YYZ-SXM

26h 40m1 stop

1:25 p.m. - 5:50 p.m.SXM-YYZ

5h 25mdirect

C$ 532Air Transat

Find Deal

Fri, 5 Dec - Sat, 13 Dec

9:10 p.m. - 1:50 p.m.YYZ-SXM

15h 40m1 stop

5:00 p.m. - 9:15 p.m.SXM-YYZ

5h 15mdirect

C$ 535Air Canada

Find Deal

Mon, 17 Nov - Fri, 21 Nov

10:15 a.m. - 4:00 p.m.YYZ-SXM

4h 45mdirect

5:00 p.m. - 9:15 p.m.SXM-YYZ

5h 15mdirect

C$ 542Air Canada

Find Deal

Wed, 17 Dec - Fri, 19 Dec

6:30 a.m. - 11:15 a.m.YYZ-SXM

4h 45mdirect

4:20 p.m. - 8:43 p.m.SXM-YYZ

5h 23mdirect

C$ 566Multiple Airlines

Find Deal

Sat, 1 Nov - Tue, 11 Nov

10:30 a.m. - 2:15 p.m.YTZ-SXM

26h 45m2 stops

1:05 p.m. - 8:50 p.m.SXM-YTZ

8h 45m1 stop

C$ 706Multiple Airlines

Find Deal

Thu, 13 Nov - Thu, 20 Nov

American Airlines flights from Toronto to Simpson Bay

Our best American Airlines deals on Toronto to Simpson Bay flight tickets

American Airlines

19 Jan

YYZ6:00 a.m.Toronto Pearson Intl

9h 28m

1 stop

SXM4:28 p.m.Simpson Bay Princess Juliana

25 Jan

SXM3:50 p.m.Simpson Bay Princess Juliana

19h 29m

1 stop

YYZ10:19 a.m.Toronto Pearson Intl

C$ 470

Find similar

American Airlines

16 Nov

YYZ4:44 p.m.Toronto Pearson Intl

20h 06m

1 stop

SXM1:50 p.m.Simpson Bay Princess Juliana

22 Nov

SXM5:05 p.m.Simpson Bay Princess Juliana

18h 12m

2 stops

YYZ10:17 a.m.Toronto Pearson Intl

C$ 479

Find similar

American Airlines

26 Jan

YYZ6:00 a.m.Toronto Pearson Intl

9h 28m

1 stop

SXM4:28 p.m.Simpson Bay Princess Juliana

3 Feb

SXM5:33 p.m.Simpson Bay Princess Juliana

19h 42m

1 stop

YYZ12:15 p.m.Toronto Pearson Intl

C$ 483

Find similar

United Airlines flights from Toronto to Simpson Bay

Our best United Airlines deals on Toronto to Simpson Bay flight tickets

United Airlines

1 Nov

YYZ7:40 p.m.Toronto Pearson Intl

20h 17m

2 stops

SXM3:57 p.m.Simpson Bay Princess Juliana

9 Nov

SXM3:00 p.m.Simpson Bay Princess Juliana

9h 59m

1 stop

YYZ11:59 p.m.Toronto Pearson Intl

C$ 466

Find similar

United Airlines

21 Feb

YYZ7:40 p.m.Toronto Pearson Intl

17h 10m

1 stop

SXM1:50 p.m.Simpson Bay Princess Juliana

28 Feb

SXM2:40 p.m.Simpson Bay Princess Juliana

20h 18m

1 stop

YYZ9:58 a.m.Toronto Pearson Intl

C$ 472

Find similar

United Airlines

9 Mar

YYZ7:40 p.m.Toronto Pearson Intl

19h 11m

2 stops

SXM2:51 p.m.Simpson Bay Princess Juliana

24 Mar

SXM3:55 p.m.Simpson Bay Princess Juliana

18h 00m

2 stops

YYZ9:55 a.m.Toronto Pearson Intl

C$ 473

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 1/11

7:40 p.m.-3:57 p.m.

2 stops20h 17m

Simpson Bay Princess Juliana

Sun 9/11

3:00 p.m.-11:59 p.m.

1 stop9h 59m

C$ 466

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 19/1

6:00 a.m.-4:28 p.m.

1 stop9h 28m

Simpson Bay Princess Juliana

Sun 25/1

3:50 p.m.-10:19 a.m.

1 stop19h 29m

C$ 470

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 15/12

9:30 a.m.-3:21 p.m.

Nonstop4h 51m

Simpson Bay Princess Juliana

Thu 18/12

4:20 p.m.-8:43 p.m.

Nonstop5h 23m

C$ 476

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Tue 16/12

9:30 a.m.-3:21 p.m.

Nonstop4h 51m

Simpson Bay Princess Juliana

Fri 19/12

4:20 p.m.-8:43 p.m.

Nonstop5h 23m

C$ 505

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Tue 3/2

5:00 p.m.-11:55 a.m.

1 stop17h 55m

Simpson Bay Princess Juliana

Tue 17/2

1:25 p.m.-5:50 p.m.

Nonstop5h 25m

C$ 531

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 5/12

8:15 a.m.-11:55 a.m.

1 stop26h 40m

Simpson Bay Princess Juliana

Sat 13/12

1:25 p.m.-5:50 p.m.

Nonstop5h 25m

C$ 532

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 17/11

9:10 p.m.-1:50 p.m.

1 stop15h 40m

Simpson Bay Princess Juliana

Fri 21/11

5:00 p.m.-9:15 p.m.

Nonstop5h 15m

C$ 535

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 17/12

10:15 a.m.-4:00 p.m.

Nonstop4h 45m

Simpson Bay Princess Juliana

Fri 19/12

5:00 p.m.-9:15 p.m.

Nonstop5h 15m

C$ 542

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 1/11

6:30 a.m.-11:15 a.m.

Nonstop4h 45m

Simpson Bay Princess Juliana

Tue 11/11

4:20 p.m.-8:43 p.m.

Nonstop5h 23m

C$ 566

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Thu 13/11

10:30 a.m.-2:15 p.m.

2 stops26h 45m

Simpson Bay Princess Juliana

Thu 20/11

1:05 p.m.-8:50 p.m.

1 stop8h 45m

C$ 706

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Toronto to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Toronto and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, October is the cheapest month to fly from Toronto to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 571. If you don’t want to visit Simpson Bay in October, then you should wait until June to fly from Toronto, when ticket prices are also cheap, with an average price of C$ 585.

What is the cheapest day to depart on your flight to Simpson Bay?

The cheapest day to depart on your flight to Simpson Bay is on a Wednesday when prices can be found for as low as C$ 639. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 747.

What is the cheapest time of day to depart on your flight to Simpson Bay?

Flying to Simpson Bay from Toronto in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 686 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around C$ 731.

What is the cheapest Toronto to Simpson Bay Princess Juliana flight route?

Fly from Toronto Pearson Intl to Simpson Bay Princess Juliana for the best Toronto - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around C$ 692 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Toronto for as low as C$ 625 on momondo.

What cabin class options are available on Toronto to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Toronto to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Simpson Bay flights?

No. A direct flight is the cheapest option for a flight between Toronto to Simpson Bay.

How have Toronto to Simpson Bay flight prices changed over time?

As of October 2025, prices for Toronto to Simpson Bay flights are approximately 2% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Toronto to Simpson Bay (YTO to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Simpson Bay

Best price found	C$ 295
Fastest flight time	4h 45m
Direct flights	Every day
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Toronto in the past 72 hours is C$ 295. The best round-trip flight deal from Toronto to Simpson Bay found on momondo in the last 72 hours is C$ 557.

The fastest flight from Toronto to Simpson Bay takes 4h 45m

Direct flights go from Toronto to Simpson Bay every day.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

Search flight deals

How far is Toronto to Simpson Bay Princess Juliana by plane?
The distance between Toronto and Simpson Bay Princess Juliana is about 3228.0 km. A reasonable flight in good conditions will take 4h 45m.
When did momondo last update prices for flights from Toronto to Simpson Bay Princess Juliana Airport?
Prices for flights from Toronto to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Toronto to Simpson Bay Princess Juliana Airport?
As of October 2025, there are 7 operators available to choose from for flights from Toronto to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Toronto to Simpson Bay Princess Juliana Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Toronto to Simpson Bay?
Based on momondo bookings for flights between Toronto and Simpson Bay, the leading plane model is Boeing 737 MAX 8, making up 60.70% of the total bookings. Other popular models include Airbus A321neo with 34.37%, Boeing 737-800 (Scimitar Winglets) with 1.97%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 0.85%.
What is the most popular airline from Toronto to Simpson Bay?
Based on momondo bookings for flights between Toronto and Simpson Bay, the leading airline is WestJet, making up 67% of the total bookings. Other popular airlines include Air Canada with 14%, United Airlines with 9%, and Air Transat with 9%.

Best airlines flying from Toronto to Simpson Bay

Compare and see reviews for airlines that fly from Toronto to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom C$ 215	Free Cancellation	Rating 7.4 8,988 reviews	Search United Airlines flights
Delta	PriceFrom C$ 345	Free Cancellation	Rating 7.9 7,979 reviews	Search Delta flights
American Airlines	PriceFrom C$ 424	Free Cancellation	Rating 7.2 11,028 reviews	Search American Airlines flights
WestJet	PriceFrom C$ 438	Free Cancellation	Rating 7.2 3,133 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 483	Free Cancellation	Rating 7.1 10,340 reviews	Search Air Canada flights
Air Transat	PriceFrom C$ 501	Free Cancellation	Rating 7.8 466 reviews	Search Air Transat flights
Caribbean Airlines	PriceFrom C$ 824	Free Cancellation	Rating 8.0 190 reviews	Search Caribbean Airlines flights

Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Simpson Bay?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Simpson Bay. momondo saves you time and could save you money on your trip.

Can I find flights from Toronto to Simpson Bay with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Toronto to Simpson Bay flights to just show those with flexible booking policies.

How can momondo help me find flights from Toronto to Simpson Bay?

Once you have performed a search for Toronto to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Toronto to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Toronto to Simpson Bay from C$ 184

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Simpson Bay departing on 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

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Filter for what you want

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American Airlines flights from Toronto to Simpson Bay

Our best American Airlines deals on Toronto to Simpson Bay flight tickets

United Airlines flights from Toronto to Simpson Bay

Our best United Airlines deals on Toronto to Simpson Bay flight tickets

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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Toronto to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Toronto and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest time of day to depart on your flight to Simpson Bay?

What is the cheapest Toronto to Simpson Bay Princess Juliana flight route?

Fly from Toronto Pearson Intl to Simpson Bay Princess Juliana for the best Toronto - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

What cabin class options are available on Toronto to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Toronto to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Simpson Bay flights?

No. A direct flight is the cheapest option for a flight between Toronto to Simpson Bay.

How have Toronto to Simpson Bay flight prices changed over time?

As of October 2025, prices for Toronto to Simpson Bay flights are approximately 2% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Toronto to Simpson Bay Princess Juliana?

United Airlines, American Airlines, and Air Canada are the most popular carriers operating from Toronto to Simpson Bay Princess Juliana

Which airlines fly to Simpson Bay?

Which airport is the most popular layover for flights between Toronto and Simpson Bay?

Miami (MIA) was the most common stop: 40% of momondo users choosing one-stop flights on this route connected there.

Which layover airport offers the lowest fares from Toronto to Simpson Bay?

Flights via Miami (MIA) offer the lowest average round-trip price of C$ 461.

Which layover airport has the shortest travel time from Toronto to Simpson Bay?

Flights connecting via Washington, D.C. (IAD) have the shortest average one-way travel time: 6h 36m.

Which layover airport has the shortest connection time from Toronto to Simpson Bay?

Washington, D.C. (IAD) has the shortest average layover time for this route: 1h 11m.

When to book flights from Toronto to Simpson Bay

Cheap Toronto to Simpson Bay (YTO to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Simpson Bay

Best price found

Fastest flight time

Direct flights

Airports in Simpson Bay

How far is Toronto to Simpson Bay Princess Juliana by plane?

When did momondo last update prices for flights from Toronto to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Toronto to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly from Toronto to Simpson Bay Princess Juliana Airport?

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular plane model from Toronto to Simpson Bay?

What is the most popular airline from Toronto to Simpson Bay?

Best airlines flying from Toronto to Simpson Bay

Compare and see reviews for airlines that fly from Toronto to Simpson Bay with momondo

Travelling to a place near Simpson Bay?

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Simpson Bay?

Can I find flights from Toronto to Simpson Bay with flexible booking policies on momondo?

How can momondo help me find flights from Toronto to Simpson Bay?

I’m not ready to book a flight from Toronto to Simpson Bay right now. Can momondo alert me if prices change?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favourite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo