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Cheap flights from Toronto to Simpson Bay from C$ 138

YTO — SXM
4 Oct — 11 Oct1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Simpson Bay Princess Juliana are usually found in June or October, booked 86 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Toronto to Simpson Bay

Enter your travel dates to find the best prices.

Cheapest flights from Toronto to Simpson Bay

Sun 29/1110:45 p.m. -
2 stops39h 00m
Sat 12/121:25 p.m. -
Nonstop5h 25m
Deal found 2/9C$ 378
Sat 14/116:30 a.m. -
Nonstop4h 45m
Tue 24/114:20 p.m. -
Nonstop5h 25m
Deal found 2/9C$ 381
Sat 7/116:30 a.m. -
Nonstop4h 45m
Sat 14/111:30 p.m. -
Nonstop5h 25m
Deal found 3/9C$ 382
Sun 25/109:50 a.m. -
Nonstop4h 55m
Fri 30/103:45 p.m. -
Nonstop5h 20m
Deal found 2/9C$ 387
Fri 13/119:30 a.m. -
Nonstop4h 55m
Fri 20/114:20 p.m. -
Nonstop5h 25m
Deal found 2/9C$ 388
Sat 7/116:30 a.m. -
Nonstop4h 45m
Sat 14/111:05 p.m. -
1 stop20h 10m
Deal found 3/9C$ 389
Thu 10/129:30 a.m. -
Nonstop4h 55m
Tue 15/124:20 p.m. -
Nonstop5h 25m
Deal found 2/9C$ 391
Thu 12/119:30 a.m. -
Nonstop4h 55m
Sat 21/111:30 p.m. -
Nonstop5h 25m
Deal found 2/9C$ 392
Tue 3/119:30 a.m. -
Nonstop4h 55m
Fri 13/114:20 p.m. -
Nonstop5h 25m
Deal found 31/8C$ 393
Sun 25/102:55 p.m. -
2 stops21h 55m
Sun 1/114:45 p.m. -
Nonstop5h 20m
Deal found 2/9C$ 395
Wed 9/125:35 p.m. -
2 stops20h 10m
Tue 15/124:45 p.m. -
Nonstop5h 20m
Deal found 2/9C$ 396
Tue 24/112:45 p.m. -
1 stop20h 10m
Tue 1/123:45 p.m. -
2 stops22h 39m
Deal found 1/9C$ 418

Find flight deals from Toronto to Simpson Bay

Round-trip from

C$ 378

One-way from

C$ 138

Popular in

December

Cheapest in

June

Average price

C$ 711

Good round-trip deal

C$ 425 or less

Good one-way deal

C$ 186 or less
Air Transat
  • Air Transat
  • 29/11-12/12
  • 2 total stops
  • 44h 25m total
  • Toronto to Simpson Bay
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WestJet
  • WestJet
  • 9/11-31/12
  • Nonstop
  • 4h 55m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Toronto (YTO) to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Toronto (YTO) to Simpson Bay Princess Juliana.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Toronto to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Mon 9/11

9:30 a.m.-3:25 p.m.

Nonstop4h 55m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 138

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Sun 4/10

9:30 a.m.-2:20 p.m.

Nonstop4h 50m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 155

TorontoSimpson Bay

YTZ Toronto Island - SXM Simpson Bay Princess Juliana

YTZSXM

Toronto Island

Thu 29/10

6:55 p.m.-1:40 p.m.

2 stops42h 45m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 177

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 29/10

10:45 p.m.-1:40 p.m.

2 stops38h 55m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 188
Quickest round-trip

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 1/10

12:20 p.m.-5:00 p.m.

Nonstop4h 40m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 193

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Fri 18/9

8:00 p.m.-12:33 p.m.

1 stop16h 33m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 208

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 17/9

9:00 p.m.-12:33 p.m.

2 stops39h 33m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 208

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 24/9

12:45 p.m.-12:33 p.m.

2 stops47h 48m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 215

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 15/10

12:20 p.m.-5:00 p.m.

Nonstop4h 40m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 215

TorontoSimpson Bay

YYZ Toronto Pearson Intl - SXM Simpson Bay Princess Juliana

YYZSXM

Toronto Pearson Intl

Thu 10/9

5:15 p.m.-12:33 p.m.

2 stops43h 18m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 218

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 36 resultsSorted by cheapest first
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Best time to book a flight from Toronto to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Toronto with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Toronto to Simpson Bay

What is the cheapest month to book a flight from Toronto to Simpson Bay?

Currently, June is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 486). Flying from Toronto to Simpson Bay in December is currently the most expensive (average of C$ 748). 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 YTO to SXM?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Toronto to Simpson Bay as you normally would.

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

Airfare is below average for this route at the moment.
Toronto to Simpson Bay flights typically cost between C$ 602 and C$ 846 in November.
The cheapest round-trip price found within the last 5 days was C$ 378 on Multiple Airlines (29 Nov-12 Dec).

What’s the top layover airport for flights from Toronto to Simpson Bay?

Montreal (YUL) – chosen by Cheapflights users on 36% of one-stop itineraries from Toronto to Simpson Bay on Cheapflights.

What’s the cheapest layover airport for flights from Toronto to Simpson Bay?

Miami (MIA) is the most affordable 1-stop option, with an average round-trip price of C$ 591.

What’s the fastest layover option from Toronto to Simpson Bay?

Flights via Newark (EWR) have the shortest average one-way travel time for 1-stop routes: 7h 13m.

Which airport typically offers the quickest layover for flights from Toronto to Simpson Bay?

Flights via Charlotte (CLT) offer the fastest connection on this route, with an average layover time of 1h 20m.

How often are flights from Toronto to Simpson Bay delayed?

About 28% of weekly flights between Toronto and Simpson Bay have experienced delays in the past year, with the average delay time being 116 minutes.

What is the most punctual flight time for Toronto to Simpson Bay flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Simpson Bay flights?

Over the past year, Air Transat has had the lowest number of delays on this route, with just 23% of flights being delayed.

How far ahead should I book a flight from Toronto to Simpson Bay?

Booking 80 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto to Simpson Bay. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Reviews of airlines servicing Simpson Bay

Check out reviews from past customers who have flown with Air Transat,United Airlines, andWestJet from Toronto to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Transat
7.8
Good
575 reviews
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
United Airlines
7.4
Good
10,162 reviews
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
WestJet
7.2
Good
3,445 reviews
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
American Airlines
7.1
Good
12,037 reviews
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus
Air Canada
7.1
Good
11,579 reviews
Air Transat
7.8
Good
575 reviews
Check prices

Food

6.8

Entertainment

7.1

Comfort

7.3

Overall

7.8

Boarding

8.0

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Paul,Jul 2026

YUL - LGW

Had to bus to the plane which made priority boarding at the back of the bus

Related info for your journey

  • What airport do you fly into for flights to Simpson Bay from Toronto?

    Located just 0.9 km from the city centre, Simpson Bay Princess Juliana is the airport most travellers will use when flying to Simpson Bay from Toronto. Booking flights from Toronto to Princess Juliana (SXM) should be relatively easy as there are 0 daily inbound flights from Toronto from 5 different airlines.

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

    United Airlines, American Airlines, and Air Transat can get you from Toronto to Simpson Bay in just under 17h 05m. Your travel time can differ by up to 3h 11m. The distance from Toronto to Simpson Bay is about 3241 km. Both multi-stop and direct flights can be found to your destination and back.

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

    Our cheapest airline available from Toronto to Simpson Bay is United Airlines. Our recent data shows that you can find tickets from as low as C$ 180 on this airline. Additional options worth looking into are Air Canada and WestJet, starting at C$ 305 and C$ 370 round-trip. United Airlines is 71% 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 to Simpson Bay one-way?

    The cheapest airlines for a one-way flight from Toronto to Simpson Bay are Air Transat (C$ 178), United Airlines (C$ 179), and Air Canada (C$ 186).

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

    The top 3 most reliable airlines when flying from Toronto to Simpson Bay are Air Canada (78%), Air Canada Rouge (78%) and WestJet (77%).

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

    Looking at all options, your cheapest flight can be booked for C$ 181. While the most popular route (Toronto Pearson Intl - Simpson Bay Princess Juliana) can be booked for C$ 329 on average, our data indicates C$ 429 when flying from Toronto to Simpson Bay.

  • Can I find deals for flights from Toronto to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Toronto to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto to Simpson Bay.

  • Can I find deals for business class flights from Toronto to Simpson Bay?

    Yes. Cheapflights offers flight deals from Toronto 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 to Simpson Bay?

    Currently, June is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 486). Flying from Toronto to Simpson Bay in December is currently the most expensive (average of C$ 748). 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

Travelling 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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Fly from Toronto to Simpson Bay on these airlines

WestJet flights from Toronto to Simpson Bay Princess Juliana
Air Transat flights from Toronto to Simpson Bay Princess Juliana

Top 5 airlines flying from Toronto to Simpson Bay

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 180AverageC$ 433FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 305AverageC$ 639FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 370AverageC$ 601FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 415AverageC$ 760FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air TransatCheapestC$ 457AverageC$ 686FlexibilityNo cancel feeOn-time50%
Search Air Transat flights

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How does Cheapflights help users find flights from Toronto to Simpson Bay?

Deals for Toronto to Simpson Bay flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Toronto to Simpson Bay?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Toronto to Simpson Bay for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Toronto to Simpson Bay with no change fees?

Yes, we can. To see specific flights from Toronto to Simpson Bay with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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Of course! You can now track prices for flights from Toronto to Simpson Bay and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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