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Cheap flights from Toronto to Simpson Bay from C$ 222

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 20/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — SXM
12 Aug — 19 Aug1
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 April, booked 52 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from Toronto to Simpson Bay

Enter your travel dates to find the best prices.

Cheapest flights from Toronto to Simpson Bay
Explore the most affordable flight options available from Toronto to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 13 July 2026.

Sun 18/109:30 a.m.
YYZ
-
SXM
Nonstop4h 50m
WestJet
Thu 22/103:10 p.m.
SXM
-
YYZ
Nonstop5h 05m
WestJet
Deal found 10/7C$ 470
Sat 19/912:20 p.m.
YYZ
-
SXM
Nonstop4h 40m
Air Canada
Sat 3/106:00 p.m.
SXM
-
YYZ
Nonstop5h 00m
Air Canada
Deal found 8/7C$ 500
Sun 20/99:30 a.m.
YYZ
-
SXM
Nonstop4h 50m
WestJet
Sun 27/93:20 p.m.
SXM
-
YYZ
Nonstop5h 05m
WestJet
Deal found 9/7C$ 507
Sat 5/912:20 p.m.
YYZ
-
SXM
Nonstop4h 40m
Air Canada
Sat 12/96:00 p.m.
SXM
-
YYZ
Nonstop5h 00m
Air Canada
Deal found 9/7C$ 510
Thu 15/109:20 a.m.
YYZ
-
SXM
Nonstop4h 50m
WestJet
Sun 18/103:20 p.m.
SXM
-
YYZ
Nonstop5h 05m
WestJet
Deal found 12/7C$ 515
Mon 31/89:30 a.m.
YYZ
-
SXM
Nonstop4h 50m
WestJet
Sun 6/93:20 p.m.
SXM
-
YYZ
Nonstop5h 05m
WestJet
Deal found 8/7C$ 525
Sun 25/109:50 a.m.
YYZ
-
SXM
Nonstop4h 55m
Air Canada
Sun 1/114:45 p.m.
SXM
-
YYZ
Nonstop5h 20m
Air Canada
Deal found 9/7C$ 529
Sun 25/109:30 a.m.
YYZ
-
SXM
Nonstop4h 51m
WestJet
Sun 1/114:20 p.m.
SXM
-
YYZ
Nonstop5h 22m
WestJet
Deal found 11/7C$ 531
Thu 26/118:55 p.m.
YTZ
-
SXM
2 stops40h 50m
Air Canada
Sat 12/123:45 p.m.
SXM
-
YTZ
1 stop18h 26m
Air Canada
Deal found 8/7C$ 653
Tue 1/128:55 p.m.
YTZ
-
SXM
1 stop14h 00m
Air Transat
Wed 9/121:05 p.m.
SXM
-
YTZ
1 stop9h 15m
Air Transat
Deal found 10/7C$ 712
Fri 20/118:30 p.m.
YTZ
-
SXM
1 stop17h 15m
Air Canada
Tue 1/123:45 p.m.
SXM
-
YTZ
1 stop17h 11m
Air Canada
Deal found 11/7C$ 742
Tue 15/128:55 p.m.
YTZ
-
SXM
1 stop14h 00m
Air Transat
Fri 18/121:05 p.m.
SXM
-
YTZ
1 stop23h 05m
Air Transat
Deal found 9/7C$ 759

Find flight deals from Toronto to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) 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 13 July 2026.

Round-trip from

C$ 470

One-way from

C$ 222

Popular in

December

Cheapest in

June

Average price

C$ 689

Good round-trip deal

C$ 567 or less

Good one-way deal

C$ 318 or less
WestJet
  • WestJet
  • 18/10-22/10
  • Nonstop
  • 9h 55m total
  • Toronto to Simpson Bay
Search Deals
WestJet
  • WestJet
  • 20/8
  • Nonstop
  • 4h 50m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Toronto (YTO) to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Simpson Bay Princess Juliana.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto 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 629,999 searches. Data last updated 13 July 2026.
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 - SXM

YYZSXM

Toronto Pearson Intl

Sat 14/11

6:45 a.m.-3:57 p.m.

1 stop8h 12m

Simpson Bay Princess Juliana

Sat 21/11

2:10 p.m.-9:47 a.m.

1 stop20h 37m

C$ 587

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Thu 26/11

8:55 p.m.-2:45 p.m.

2 stops40h 50m

Simpson Bay Princess Juliana

Sat 12/12

3:45 p.m.-3:04 p.m.

2 stops24h 19m

C$ 655

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Tue 1/12

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

1 stop14h 00m

Simpson Bay Princess Juliana

Wed 9/12

1:05 p.m.-9:20 p.m.

1 stop9h 15m

C$ 712

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 24/10

9:44 a.m.-12:50 p.m.

2 stops27h 06m

Simpson Bay Princess Juliana

Sat 31/10

4:00 p.m.-11:52 p.m.

1 stop7h 52m

C$ 780

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Sat 14/11

8:30 p.m.-1:50 p.m.

2 stops40h 20m

Simpson Bay Princess Juliana

Sat 21/11

3:45 p.m.-11:56 a.m.

1 stop21h 11m

C$ 854

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 23/7

10:15 a.m.-12:33 p.m.

2 stops26h 18m

Simpson Bay Princess Juliana

Tue 28/7

3:50 p.m.-11:49 a.m.

2 stops19h 59m

C$ 879

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Thu 15/10

7:55 p.m.-11:20 a.m.

1 stop15h 25m

Simpson Bay Princess Juliana

Fri 23/10

12:30 p.m.-7:55 a.m.

1 stop19h 25m

C$ 895

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Wed 25/11

3:35 p.m.-2:45 p.m.

2 stops22h 10m

Simpson Bay Princess Juliana

Sat 28/11

3:45 p.m.-7:56 a.m.

1 stop17h 11m

C$ 902

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 30/7

8:45 a.m.-12:33 p.m.

2 stops27h 48m

Simpson Bay Princess Juliana

Thu 6/8

3:50 p.m.-3:46 p.m.

2 stops23h 56m

C$ 946

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 1/10

8:30 a.m.-11:33 a.m.

1 stop27h 03m

Simpson Bay Princess Juliana

Sun 11/10

12:32 p.m.-1:13 a.m.

1 stop12h 41m

C$ 975

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 39 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
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 to Simpson Bay

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

Currently, November is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 176). Flying from Toronto to Simpson Bay in March is currently the most expensive (average of C$ 1,629). 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?

Find hourly flight availability from Toronto 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 13 July 2026.

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?

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

Share of one-stop round-trip flights from Toronto to Simpson Bay chosen by Cheapflights users in the past 12 months, using the same layover each way.

Montreal (YUL) – chosen by Cheapflights users on 20% of one-stop itineraries from Toronto to Simpson Bay on Cheapflights.

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

Average round-trip fare for 1-stop flights from Toronto to Simpson Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Chicago (ORD) is the most affordable 1-stop option, with an average round-trip price of C$ 482.

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

Shortest average travel time for 1-stop one-way flights from Toronto to Simpson Bay, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Charlotte (CLT) have the shortest average one-way travel time for 1-stop routes: 7h 32m.

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

Average layover duration for 1-stop one-way flights from Toronto to Simpson Bay, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

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 29% of weekly flights between Toronto and Simpson Bay have experienced delays in the past year, with the average delay time being 117 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 22% of flights being delayed.

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

Booking 50 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

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 13 July 2026.
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
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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
564 reviews
Air Transat
7.8
Good
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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
9,988 reviews
Air Transat
7.8
Good
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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
3,410 reviews
Air Transat
7.8
Good
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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
11,811 reviews
Air Transat
7.8
Good
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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
11,336 reviews
Air Transat
7.8
Good
564 reviews
Check prices

Comfort

7.3

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

Boarding

8.0

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

Find useful and relevant information for your journey from Toronto 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?

    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 6 different airlines.

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

    United Airlines, Air Canada, and Air Transat can get you from Toronto to Simpson Bay in just under 8h 12m. Your travel time can differ by up to 32h 38m. 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$ 185 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at C$ 313 and C$ 362 round-trip. United Airlines is 72% 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$ 183), United Airlines (C$ 184), and WestJet (C$ 195).

  • 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 WestJet (83%), Air Canada (75%) and Air Canada Rouge (50%).

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

    Looking at all options, your cheapest flight can be booked for C$ 246. While the most popular route (Toronto Pearson Intl - Simpson Bay Princess Juliana) can be booked for C$ 561 on average, our data indicates C$ 500 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, November is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 176). Flying from Toronto to Simpson Bay in March is currently the most expensive (average of C$ 1,629). 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

Choose from the following airlines for your flight from Toronto to Simpson Bay. Flights are based on user searches made on Cheapflights and were last updated on 13 July 2026.
WestJet flights from Toronto to Simpson Bay Princess Juliana
Air Transat flights from Toronto to Simpson Bay Princess Juliana

Top 6 airlines flying from Toronto to Simpson Bay

Discover the top 6 airlines that operate flights from Toronto 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 629,999 searches. Data last updated 13 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 185AverageC$ 548FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 313AverageC$ 661FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 362AverageC$ 748FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 390AverageC$ 643FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air TransatCheapestC$ 519AverageC$ 709FlexibilityNo cancel feeOn-time50%
Search Air Transat flights
DeltaCheapestC$ 743AverageC$ 786FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

Can Cheapflights notify me if prices for flights from Toronto to Simpson Bay become cheaper?

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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