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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 Cheapflights user in the last 72 hours by searching for a flight departing on 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — SXM
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Toronto to Simpson Bay Princess Juliana are usually found in October or June, booked 24 days in advance, depart on a Wednesday or Monday and return on a Friday

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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 3 November 2025.

Mon 10/115:15 p.m.YYZ - SXM
2 stops22h 07mAmerican Airlines
Thu 20/115:24 p.m.SXM - YYZ
2 stops17h 25mAmerican Airlines
Deal found 1/11C$ 489
Sun 7/129:30 a.m.YYZ - SXM
Nonstop4h 51mMultiple Airlines
Tue 16/123:40 p.m.SXM - YYZ
1 stop9h 24mMultiple Airlines
Deal found 3/11C$ 495
Mon 10/113:49 p.m.YYZ - SXM
2 stops23h 33mAmerican Airlines
Thu 11/125:25 p.m.SXM - YYZ
2 stops29h 05mAmerican Airlines
Deal found 1/11C$ 496
Mon 1/129:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Mon 8/124:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Deal found 1/11C$ 500
Sun 14/126:00 p.m.YYZ - SXM
1 stop16h 55mAir Transat
Sat 20/121:25 p.m.SXM - YYZ
Nonstop5h 25mAir Transat
Deal found 1/11C$ 503
Sun 14/126:50 a.m.YYZ - SXM
1 stop8h 07mUnited Airlines
Fri 19/124:55 p.m.SXM - YYZ
1 stop7h 51mUnited Airlines
Deal found 1/11C$ 509
Tue 11/116:00 a.m.YYZ - SXM
1 stop9h 22mAmerican Airlines
Wed 19/115:24 p.m.SXM - YYZ
2 stops17h 53mAmerican Airlines
Deal found 1/11C$ 511
Wed 12/1110:10 a.m.YYZ - SXM
2 stops26h 40mMultiple Airlines
Thu 20/114:20 p.m.SXM - YYZ
Nonstop5h 23mMultiple Airlines
Deal found 1/11C$ 514
Sat 13/126:30 a.m.YYZ - SXM
Nonstop4h 45mAir Transat
Sat 20/121:25 p.m.SXM - YYZ
Nonstop5h 25mAir Transat
Deal found 2/11C$ 516
Mon 10/114:20 p.m.YTZ - SXM
2 stops20h 30mAir Canada
Thu 20/113:40 p.m.SXM - YTZ
1 stop19h 15mAir Canada
Deal found 1/11C$ 537
Sun 2/116:30 p.m.YTZ - SXM
2 stops42h 20mAir Canada
Thu 6/112:52 p.m.SXM - YTZ
2 stops28h 03mAir Canada
Deal found 2/11C$ 539
Fri 12/128:30 p.m.YTZ - SXM
1 stop17h 10mMultiple Airlines
Mon 15/121:05 p.m.SXM - YTZ
1 stop29h 20mMultiple Airlines
Deal found 1/11C$ 548

Cheap 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 3 November 2025.

Round-trip from

C$ 483

One-way from

C$ 184

Popular in

December

Cheapest in

October

Average price

C$ 595

Good round-trip deal

C$ 563 or less

Good one-way deal

C$ 294 or less
WestJet
  • WestJet
  • 14/11-20/11
  • Nonstop
  • 10h 14m total
  • Toronto to Simpson Bay
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United Airlines
  • United Airlines
  • 6/12
  • 2 total stops
  • 16h 38m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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.
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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 3 November 2025.
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

Sun 14/12

6:50 a.m.-3:57 p.m.

1 stop8h 07m

Simpson Bay Princess Juliana

Fri 19/12

4:55 p.m.-11:46 p.m.

1 stop7h 51m

C$ 509

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 14/12

8:40 a.m.-11:55 a.m.

1 stop26h 15m

Simpson Bay Princess Juliana

Sat 20/12

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

Nonstop5h 25m

C$ 511

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 14/12

6:50 a.m.-3:57 p.m.

1 stop8h 07m

Simpson Bay Princess Juliana

Sat 20/12

5:00 p.m.-11:46 p.m.

1 stop7h 46m

C$ 524

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Wed 25/3

8:00 a.m.-10:55 a.m.

1 stop26h 55m

Simpson Bay Princess Juliana

Thu 2/4

12:05 p.m.-8:50 p.m.

1 stop8h 45m

C$ 525

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Tue 24/3

8:00 a.m.-10:55 a.m.

1 stop26h 55m

Simpson Bay Princess Juliana

Thu 2/4

12:05 p.m.-8:50 p.m.

1 stop8h 45m

C$ 525

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Tue 24/3

8:00 a.m.-10:55 a.m.

1 stop26h 55m

Simpson Bay Princess Juliana

Wed 1/4

12:05 p.m.-8:50 p.m.

1 stop8h 45m

C$ 525

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Tue 23/12

6:30 a.m.-12:15 p.m.

Nonstop4h 45m

Simpson Bay Princess Juliana

Tue 30/12

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

Nonstop5h 25m

C$ 525

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Sun 29/3

8:55 p.m.-1:35 p.m.

2 stops40h 40m

Simpson Bay Princess Juliana

Sat 4/4

2:40 p.m.-8:51 a.m.

1 stop18h 11m

C$ 531

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 18/1

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

Nonstop4h 51m

Simpson Bay Princess Juliana

Sun 25/1

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

Nonstop5h 23m

C$ 535

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Wed 25/3

4:30 p.m.-10:55 a.m.

1 stop18h 25m

Simpson Bay Princess Juliana

Wed 1/4

12:05 p.m.-9:50 p.m.

1 stop9h 45m

C$ 549

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/10

Showing 1-10 of 36 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 31 October 2025.

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, November is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 247). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 516). 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 3 November 2025.

When flying from Toronto to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 68% versus a flight in the evening.

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 38% 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$ 502.

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 19m.

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 16m.

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 3 November 2025.
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
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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
470 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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.
United Airlines
7.4
Good
8,996 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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
11,036 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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
3,153 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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
10,394 reviews
Air Transat
7.8
Good
470 reviews
Check prices

Entertainment

7.1

Boarding

7.9

Comfort

7.4

Food

6.8

Overall

7.8

Crew

8.5

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 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 7 different airlines.

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

    United Airlines, Air Transat, and Air Canada can get you from Toronto to Simpson Bay in just under 8h 07m. Your travel time can differ by up to 32h 33m. 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$ 261 on this airline. Additional options worth looking into are Delta and American Airlines, starting at C$ 345 and C$ 423 round-trip. United Airlines is 61% 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$ 184), Air Transat (C$ 269), and Air Canada (C$ 283).

  • 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 (100%), WestJet (73%) and Air Canada (50%).

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

    Looking at all options, your cheapest flight can be booked for C$ 252. While the most popular route (Toronto Pearson Intl - Simpson Bay Princess Juliana) can be booked for C$ 380 on average, our data indicates C$ 525 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$ 247). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 516). 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 3 November 2025.
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 3 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 261AverageC$ 566FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 345AverageC$ 778FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 423AverageC$ 622FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 436AverageC$ 675FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 484AverageC$ 727FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 500AverageC$ 748FlexibilityNo cancel feeOn-time50%
Search Air Transat flights
Caribbean AirlinesCheapestC$ 823AverageC$ 969FlexibilityNo cancel feeOn-timeN/A
Search Caribbean Airlines 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.

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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