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Cheap flights from Toronto to Simpson Bay from C$ 201

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 16/3. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — SXM
22 Jan — 29 Jan1
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 23 December 2025.

Wed 24/123:30 p.m.YYZ - SXM
2 stops21h 20mUnited Airlines
Wed 31/124:55 p.m.SXM - YYZ
1 stop7h 51mUnited Airlines
Deal found 21/12C$ 526
Tue 23/129:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Tue 30/124:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Deal found 22/12C$ 599
Wed 24/123:30 p.m.YYZ - SXM
2 stops21h 20mUnited Airlines
Tue 30/124:55 p.m.SXM - YYZ
1 stop27h 02mUnited Airlines
Deal found 21/12C$ 642
Wed 24/127:30 a.m.YYZ - SXM
1 stop28h 56mAmerican Airlines
Sun 28/123:28 p.m.SXM - YYZ
1 stop21h 57mAmerican Airlines
Deal found 22/12C$ 665
Tue 23/126:20 a.m.YYZ - SXM
1 stop7h 20mMultiple Airlines
Tue 30/121:25 p.m.SXM - YYZ
Nonstop5h 25mMultiple Airlines
Deal found 22/12C$ 672
Tue 23/126:30 a.m.YYZ - SXM
Nonstop4h 45mAir Transat
Tue 30/121:25 p.m.SXM - YYZ
Nonstop5h 25mAir Transat
Deal found 22/12C$ 673
Sun 21/125:30 p.m.YYZ - SXM
2 stops21h 21mUnited Airlines
Wed 31/124:55 p.m.SXM - YYZ
1 stop7h 51mUnited Airlines
Deal found 21/12C$ 679
Mon 29/128:00 a.m.YYZ - SXM
1 stop29h 40mAir Canada
Wed 7/15:00 p.m.SXM - YYZ
Nonstop5h 15mAir Canada
Deal found 22/12C$ 710
Wed 24/129:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Tue 30/124:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Deal found 21/12C$ 743
Sun 21/127:10 p.m.YYZ - SXM
1 stop17h 49mAmerican Airlines
Wed 31/121:39 p.m.SXM - YYZ
1 stop11h 10mAmerican Airlines
Deal found 21/12C$ 756
Mon 22/128:30 a.m.YTZ - SXM
1 stop29h 10mAir Canada
Thu 1/13:40 p.m.SXM - YTZ
1 stop19h 15mAir Canada
Deal found 21/12C$ 909
Wed 24/1210:30 a.m.YTZ - SXM
1 stop27h 10mAir Canada
Sun 28/123:40 p.m.SXM - YTZ
1 stop29h 15mAir Canada
Deal found 22/12C$ 1,199

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 23 December 2025.

Round-trip from

C$ 412

One-way from

C$ 201

Popular in

December

Cheapest in

June

Average price

C$ 845

Good round-trip deal

C$ 492 or less

Good one-way deal

C$ 398 or less
United Airlines
  • United Airlines
  • 1/3-11/3
  • 4 total stops
  • 35h 13m total
  • Toronto to Simpson Bay
Search Deals
United Airlines
  • United Airlines
  • 16/3
  • 2 total stops
  • 24h 06m 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$ 23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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.
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 23 December 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

Thu 15/1

9:00 p.m.-1:50 p.m.

2 stops39h 50m

Simpson Bay Princess Juliana

Sun 18/1

4:55 p.m.-2:20 p.m.

2 stops22h 25m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 8/2

10:00 a.m.-1:50 p.m.

2 stops26h 50m

Simpson Bay Princess Juliana

Sun 15/2

4:55 p.m.-11:48 a.m.

2 stops19h 53m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/3

7:40 p.m.-1:50 p.m.

2 stops17h 10m

Simpson Bay Princess Juliana

Tue 10/3

3:55 p.m.-9:58 a.m.

2 stops18h 03m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 19/1

7:40 p.m.-1:50 p.m.

2 stops17h 10m

Simpson Bay Princess Juliana

Sun 25/1

4:55 p.m.-1:43 p.m.

2 stops21h 48m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 22/1

9:00 p.m.-1:50 p.m.

2 stops39h 50m

Simpson Bay Princess Juliana

Wed 28/1

2:52 p.m.-2:14 p.m.

2 stops24h 22m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/3

7:40 p.m.-1:50 p.m.

2 stops17h 10m

Simpson Bay Princess Juliana

Fri 6/3

4:55 p.m.-9:58 a.m.

2 stops18h 03m

C$ 412

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 17/1

3:30 p.m.-1:50 p.m.

2 stops21h 20m

Simpson Bay Princess Juliana

Sun 25/1

4:55 p.m.-2:14 p.m.

1 stop22h 19m

C$ 412

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Mon 19/1

6:30 p.m.-2:40 p.m.

1 stop19h 10m

Simpson Bay Princess Juliana

Sun 25/1

3:40 p.m.-11:55 a.m.

1 stop21h 15m

C$ 501

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Wed 14/1

8:30 a.m.-2:40 p.m.

1 stop29h 10m

Simpson Bay Princess Juliana

Tue 20/1

3:40 p.m.-11:42 a.m.

2 stops21h 02m

C$ 503

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Thu 22/1

10:25 a.m.-1:50 p.m.

2 stops26h 25m

Simpson Bay Princess Juliana

Tue 27/1

3:40 p.m.-6:13 p.m.

2 stops27h 33m

C$ 537

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/12

Showing 1-10 of 28 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 19 December 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, March is the cheapest month in which you can book a flight from Toronto to Simpson Bay (average of C$ 295). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 507). 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 23 December 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.

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 23 December 2025.

The most flights from YTO to SXM are scheduled on a Tuesday (3 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 42% 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$ 447.

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 41m.

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 19% of weekly flights between Toronto and Simpson Bay have experienced delays in the past year, with the average delay time being 128 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 11% 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 23 December 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
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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
484 reviews
Air Transat
7.8
Good
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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
9,106 reviews
Air Transat
7.8
Good
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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
11,050 reviews
Air Transat
7.8
Good
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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
3,216 reviews
Air Transat
7.8
Good
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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
10,551 reviews
Air Transat
7.8
Good
484 reviews
Check prices

Boarding

7.9

Food

6.8

Comfort

7.4

Entertainment

7.1

Overall

7.8

Crew

8.4

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 2 daily inbound flights from Toronto from 7 different airlines.

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

    United Airlines and Air Canada can get you from Toronto to Simpson Bay in just under 19h 10m. Your travel time can differ by up to 20h 40m. The distance from Toronto to Simpson Bay is about 3227 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$ 211 on this airline. Additional options worth looking into are American Airlines and WestJet, starting at C$ 324 and C$ 394 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 WestJet (C$ 170), United Airlines (C$ 180), and American Airlines (C$ 183).

  • 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 (87%), Air Transat (57%) and Air Canada (56%).

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

    Looking at all options, your cheapest flight can be booked for C$ 188. While the most popular route (Toronto Pearson Intl - Simpson Bay Princess Juliana) can be booked for C$ 412 on average, our data indicates C$ 615 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$ 295). Flying from Toronto to Simpson Bay in August is currently the most expensive (average of C$ 507). 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 23 December 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 23 December 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 349AverageC$ 559FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 399AverageC$ 595FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 408AverageC$ 651FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 480AverageC$ 703FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Air TransatCheapestC$ 503AverageC$ 729FlexibilityNo cancel feeOn-time50%
Search Air Transat flights
DeltaCheapestC$ 633AverageC$ 765FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Caribbean AirlinesCheapestC$ 809AverageC$ 958FlexibilityNo 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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