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Cheap flights from Toronto to Simpson Bay from C$ 159

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 31/3. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — SXM
20 Mar — 27 Mar1
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 24 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 18 February 2026.

Sat 25/48:50 a.m.
YYZ
-
SXM
1 stop7h 59m
United Airlines
Wed 29/43:50 p.m.
SXM
-
YYZ
2 stops19h 53m
United Airlines
Deal found 18/2C$ 454
Wed 4/312:10 p.m.
YYZ
-
SXM
2 stops25h 30m
Air Canada
Wed 11/31:52 p.m.
SXM
-
YYZ
2 stops21h 48m
Air Canada
Deal found 18/2C$ 455
Mon 2/38:05 p.m.
YYZ
-
SXM
1 stop16h 45m
Air Canada
Wed 11/31:52 p.m.
SXM
-
YYZ
2 stops21h 48m
Air Canada
Deal found 17/2C$ 456
Sat 18/48:50 a.m.
YYZ
-
SXM
1 stop7h 59m
United Airlines
Wed 22/41:35 p.m.
SXM
-
YYZ
1 stop8h 48m
United Airlines
Deal found 18/2C$ 461
Mon 2/37:10 p.m.
YYZ
-
SXM
1 stop18h 06m
American Airlines
Wed 11/34:28 p.m.
SXM
-
YYZ
2 stops18h 28m
American Airlines
Deal found 17/2C$ 463
Sun 12/49:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
WestJet
Thu 16/43:20 p.m.
SXM
-
YYZ
Nonstop5h 22m
WestJet
Deal found 15/2C$ 466
Fri 6/310:15 a.m.
YYZ
-
SXM
Nonstop4h 45m
Air Canada
Thu 12/31:52 p.m.
SXM
-
YYZ
1 stop19h 44m
Air Canada
Deal found 14/2C$ 467
Tue 3/36:00 a.m.
YYZ
-
SXM
1 stop7h 16m
American Airlines
Tue 10/34:01 p.m.
SXM
-
YYZ
1 stop18h 17m
American Airlines
Deal found 15/2C$ 469
Tue 24/39:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
WestJet
Tue 31/33:20 p.m.
SXM
-
YYZ
Nonstop5h 22m
WestJet
Deal found 17/2C$ 470
Tue 3/36:30 a.m.
YYZ
-
SXM
Nonstop4h 45m
Air Transat
Tue 10/312:25 p.m.
SXM
-
YYZ
Nonstop5h 25m
Air Transat
Deal found 17/2C$ 471
Mon 2/312:30 p.m.
YTZ
-
SXM
2 stops24h 20m
Air Canada
Wed 11/31:52 p.m.
SXM
-
YTZ
2 stops24h 33m
Air Canada
Deal found 18/2C$ 473
Mon 27/47:43 p.m.
YYZ
-
SXM
2 stops16h 50m
United Airlines
Thu 7/51:35 p.m.
SXM
-
YYZ
2 stops20h 29m
United Airlines
Deal found 17/2C$ 473

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 18 February 2026.

Round-trip from

C$ 454

One-way from

C$ 159

Popular in

December

Cheapest in

June

Average price

C$ 749

Good round-trip deal

C$ 520 or less

Good one-way deal

C$ 219 or less
United Airlines
  • United Airlines
  • 25/4-29/4
  • 2 total stops
  • 26h 13m total
  • Toronto to Simpson Bay
Search Deals
Air Transat
  • Air Transat
  • 24/3
  • 1 total stop
  • 21h 00m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 18 February 2026.
Use the filters below to find and compare flights from Toronto to Simpson Bay that are best for you.

Fly from

Toronto

Fly to

Simpson Bay

Route

Depart

Return

Price

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 11/4

8:50 a.m.-4:49 p.m.

1 stop7h 59m

Simpson Bay Princess Juliana

Sat 18/4

3:50 p.m.-10:04 a.m.

1 stop18h 14m

C$ 454

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 25/4

8:50 a.m.-4:49 p.m.

1 stop7h 59m

Simpson Bay Princess Juliana

Wed 29/4

3:50 p.m.-10:04 a.m.

1 stop18h 14m

C$ 454

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 18/4

8:50 a.m.-4:49 p.m.

1 stop7h 59m

Simpson Bay Princess Juliana

Wed 22/4

1:35 p.m.-10:23 p.m.

1 stop8h 48m

C$ 461

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Mon 2/3

12:30 p.m.-1:50 p.m.

2 stops24h 20m

Simpson Bay Princess Juliana

Wed 11/3

1:52 p.m.-2:25 p.m.

2 stops24h 33m

C$ 473

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 11/3

11:10 p.m.-10:55 a.m.

1 stop11h 45m

Simpson Bay Princess Juliana

Sat 14/3

12:25 p.m.-5:50 p.m.

Nonstop5h 25m

C$ 474

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 27/4

7:43 p.m.-12:33 p.m.

2 stops16h 50m

Simpson Bay Princess Juliana

Thu 7/5

1:35 p.m.-10:04 a.m.

2 stops20h 29m

C$ 474

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 28/5

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

1 stop23h 48m

Simpson Bay Princess Juliana

Wed 3/6

3:50 p.m.-9:54 a.m.

2 stops18h 04m

C$ 476

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 2/5

7:43 p.m.-12:33 p.m.

2 stops16h 50m

Simpson Bay Princess Juliana

Tue 12/5

1:35 p.m.-7:02 p.m.

2 stops29h 27m

C$ 476

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 28/5

9:44 a.m.-12:33 p.m.

1 stop26h 49m

Simpson Bay Princess Juliana

Thu 4/6

3:50 p.m.-9:54 a.m.

2 stops18h 04m

C$ 476

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 28/5

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

2 stops26h 18m

Simpson Bay Princess Juliana

Tue 2/6

3:50 p.m.-11:54 p.m.

1 stop8h 04m

C$ 476

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/2

Showing 1-10 of 33 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Simpson Bay. Price data was last updated on 18 February 2026.

Booking 24 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.

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

Currently, March is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 238). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 484). 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 18 February 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.

Weekly flight availability from Toronto to Simpson Bay

Explore weekly flight availability from Toronto to Simpson Bay. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 18 February 2026.

The most flights from YTO to SXM are scheduled on a Tuesday (4 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

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.

Newark (EWR) – chosen by Cheapflights users on 48% 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$ 450.

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 Washington, D.C. (IAD) have the shortest average one-way travel time for 1-stop routes: 6h 43m.

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 23m.

How often are flights from Toronto to Simpson Bay delayed?

About 23% of weekly flights between Toronto and Simpson Bay have experienced delays in the past year, with the average delay time being 130 minutes.

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

Historically, flights departing in the morning 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 Wednesday 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 16% of flights being delayed.

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 18 February 2026.
Check out reviews from past customers who have flown with Air Transat,United Airlines, andAmerican Airlines 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
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Transat
7.7
Good
509 reviews
Air Transat
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
United Airlines
7.4
Good
9,322 reviews
Air Transat
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
American Airlines
7.2
Good
11,313 reviews
Air Transat
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
WestJet
7.2
Good
3,268 reviews
Air Transat
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.
Air Canada
7.1
Good
10,732 reviews
Air Transat
7.7
Good
509 reviews
Check prices

Crew

8.4

Comfort

7.3

Food

6.8

Boarding

7.9

Overall

7.7

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Dec 2025

YOW - GCM

The flight was delayed for 3.5 hours. No compensation for a meal voucher. We were positioned at the back of the plane and the toilets were not working properly. It was a foul smell coming from the toilet.

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 2 daily inbound flights from Toronto from 7 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 7h 59m. Your travel time can differ by up to 16h 21m. 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$ 208 on this airline. Additional options worth looking into are Air Canada and WestJet, starting at C$ 302 and C$ 395 round-trip. United Airlines is 68% 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 United Airlines (C$ 177), WestJet (C$ 179), and Air Canada (C$ 205).

  • 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 Transat (75%), Air Canada (44%) and WestJet (40%).

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

    Looking at all options, your cheapest flight can be booked for C$ 204. While the most popular route (Toronto Pearson Intl - Simpson Bay Princess Juliana) can be booked for C$ 392 on average, our data indicates C$ 443 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, March is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 238). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 484). 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

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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 18 February 2026.
WestJet flights from Toronto to Simpson Bay Princess Juliana
Air Transat flights from Toronto to Simpson Bay Princess Juliana

Top 7 airlines flying from Toronto to Simpson Bay

Discover the top 7 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 18 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 208AverageC$ 545FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 302AverageC$ 712FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 395AverageC$ 643FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 396AverageC$ 606FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air TransatCheapestC$ 500AverageC$ 716FlexibilityNo cancel feeOn-time50%
Search Air Transat flights
DeltaCheapestC$ 628AverageC$ 759FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Caribbean AirlinesCheapestC$ 911AverageC$ 951FlexibilityNo cancel feeOn-timeN/A
Search Caribbean Airlines 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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