YYZ - SXM

C$ 184 Find Cheap Flights from Toronto to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto to Simpson Bay departing on 8/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Simpson Bay.
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Everything you should know

Cheapest round-trip
C$ 459
Overall average: C$ 566
WestJet
Thu 9/4Thu 16/4
YYZ - SXM • Direct
Cheapest one-way flights
C$ 180
Typical prices: C$ 257-C$ 425
United Airlines
Sun 8/2
YYZ - SXM • 1 stop
Our travellers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Air Canada's Preferred Economy adds 10 cm of legroom.
WestJet's bidding on upgrades can save on Premium fares.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from C$ 459 (round-trip)
Air Transat
Best reviews • 7.7 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 12% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 13% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Toronto to Simpson Bay (YYZ-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto to Simpson Bay

Thu, 9 Apr - Thu, 16 Apr
WestJet Logo
9:30 a.m. - 2:17 p.m.
YYZ
-
SXM
4h 47mdirect
WestJet Logo
3:20 p.m. - 8:42 p.m.
SXM
-
YYZ
5h 22mdirect
C$ 459WestJet
Sun, 8 Mar - Mon, 16 Mar
American Airlines Logo
4:30 p.m. - 11:29 a.m.
YYZ
-
SXM
18h 59m
2 stops
American Airlines Logo
4:01 p.m. - 10:18 a.m.
SXM
-
YYZ
18h 17m
1 stop
C$ 461American Airlines
Sun, 8 Mar - Mon, 16 Mar
American Airlines Logo
7:10 p.m. - 1:21 p.m.
YYZ
-
SXM
18h 11m
2 stops
American Airlines Logo
4:01 p.m. - 10:18 a.m.
SXM
-
YYZ
18h 17m
1 stop
C$ 462American Airlines
Wed, 18 Mar - Mon, 6 Apr
Air Canada Logo
7:30 a.m. - 2:51 p.m.
YYZ
-
SXM
7h 21m
1 stop
Air Canada Logo
4:00 p.m. - 9:00 p.m.
SXM
-
YYZ
5h 00mdirect
C$ 463Air Canada
Mon, 9 Mar - Mon, 6 Apr
Air Canada Logo
7:30 a.m. - 2:51 p.m.
YYZ
-
SXM
7h 21m
1 stop
Air Canada Logo
4:00 p.m. - 9:00 p.m.
SXM
-
YYZ
5h 00mdirect
C$ 465Air Canada
Tue, 24 Feb - Tue, 3 Mar
American Airlines Logo
6:00 a.m. - 2:16 p.m.
YYZ
-
SXM
7h 16m
1 stop
American Airlines Logo
5:01 p.m. - 10:19 a.m.
SXM
-
YYZ
18h 18m
1 stop
C$ 466American Airlines
Sat, 21 Feb - Tue, 3 Mar
American Airlines Logo
6:15 p.m. - 4:00 p.m.
YYZ
-
SXM
20h 45m
1 stop
American Airlines Logo
5:01 p.m. - 10:19 a.m.
SXM
-
YYZ
18h 18m
1 stop
C$ 467American Airlines
Thu, 9 Apr - Thu, 16 Apr
American Airlines Logo
5:25 p.m. - 1:21 p.m.
YYZ
-
SXM
19h 56m
2 stops
American Airlines Logo
2:24 p.m. - 10:29 a.m.
SXM
-
YYZ
20h 05m
2 stops
C$ 469American Airlines
Wed, 18 Mar - Mon, 6 Apr
Multiple Airlines Logo
9:30 a.m. - 2:17 p.m.
YYZ
-
SXM
4h 47mdirect
Multiple Airlines Logo
4:00 p.m. - 9:00 p.m.
SXM
-
YYZ
5h 00mdirect
C$ 470Multiple Airlines
Tue, 24 Feb - Tue, 3 Mar
American Airlines Logo
7:30 a.m. - 4:00 p.m.
YYZ
-
SXM
7h 30m
1 stop
American Airlines Logo
4:01 p.m. - 10:59 a.m.
SXM
-
YYZ
19h 58m
2 stops
C$ 471American Airlines
Booking Insights

KAYAK's insights & trends for Toronto to Simpson Bay flights

Get data-powered insights and trends into flights from Toronto to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Toronto to Simpson Bay?

The average price of all round-trip flights from Toronto Pearson Intl Airport to Simpson Bay clicked on KAYAK for each day over the last 12 months.

When flying from Toronto to Simpson Bay, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Toronto, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Simpson Bay is April, where tickets cost C$ 566 (return) on average. On the other hand, the most expensive months are August and February, where the average cost of round-trip tickets is C$ 776 and C$ 737 respectively.

Can I save money by flying with a layover from Toronto Pearson Intl Airport to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at C$ 543 on average.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Simpson Bay?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto Pearson Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Toronto Pearson Intl Airport to Simpson Bay, you should book around 2 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Expert advice

Expert advice for your flight from Toronto to Simpson Bay

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet and Air Canada

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

John Walton

John Walton

Expert on Air Transat

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Good to know

Low seasonOctober
Cheapest flightC$ 180
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (13% more expensive on average)
Flight from Toronto to Simpson Bay

When to book flights from Toronto to Simpson Bay

Are your dates flexible? Find out the best times to travel from Toronto to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto to Simpson Bay flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Simpson Bay was C$ 180 for a one-way ticket and C$ 459 for a round-trip.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Simpson Bay?

    Air Canada, and WestJet offer inflight Wi-Fi service on the Toronto to Simpson Bay flight route.

  • Which aircraft models fly most regularly from Toronto to Simpson Bay?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Toronto to Simpson Bay flight route.

  • Which airline alliances offer flights from Toronto to Simpson Bay?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Toronto and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Toronto to Simpson Bay?

    There are direct flights from Toronto to Simpson Bay on a daily basis.

  • Which is the best airline for flights from Toronto to Simpson Bay, Delta or Caribbean Airlines?

    The two airlines most popular with KAYAK users for flights from Toronto to Simpson Bay are Delta and Caribbean Airlines. With an average price for the route of C$ 753 and an overall rating of 7.9, Delta is the most popular choice. Caribbean Airlines is also a great choice for the route, with an average price of C$ 942 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Toronto to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Toronto is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Toronto with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Pearson Intl Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 261 or less one-way and C$ 506 or less round-trip.

Prefer to fly direct from Toronto to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Pearson Intl to Simpson Bay Princess Juliana.
Find which airlines fly direct from Toronto Pearson Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Toronto Pearson Intl to Simpson Bay Princess Juliana

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

Air Canada,Air Transat,WestJet

Air Canada,Air Transat, +1 more

Wednesday

Air Canada,WestJet

Air Canada,WestJet

Thursday

WestJet

WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Canada,Air Transat

Air Canada,Air Transat

Sunday

WestJet

WestJet

See more nonstop flights

Direct returns

Simpson Bay Princess Juliana to Toronto Pearson Intl

Monday

Air Canada,WestJet

Air Canada,WestJet

Tuesday

Air Canada,Air Transat,WestJet

Air Canada,Air Transat, +1 more

Wednesday

Air Canada,WestJet

Air Canada,WestJet

Thursday

WestJet

WestJet

Friday

Air Canada,WestJet

Air Canada,WestJet

Saturday

Air Canada,Air Transat

Air Canada,Air Transat

Sunday

WestJet

WestJet

See more nonstop flights

Reviews of the top 5 airlines flying from Toronto to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.7
Air TransatOverall score based on 502 reviews
7.0Entertainment
7.3Comfort
7.9Boarding
6.8Food
8.4Crew
Airline reviews

The Turkish was good . I had a problem with air Transat terrible experience for me

2.0 MediocreAnonymous, Jan 2026
IST - YYZ
Read more Air Transat reviews

The Turkish was good . I had a problem with air Transat terrible experience for me

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Everything was horrible. On the day of my departure, I was denied check-in and boarding because my reservation only showed one of my last names, while my passport contains both. This minor discrepancy could have been easily corrected, but I was informed that no adjustment could be made. As a result, I lost not only my outbound flight but also my return flight and had to purchase a new ticket at a significantly higher cost.

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight to London from Philadelphia was cancelled due to weather.

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Good service, friendly staff. Food was average for airlines and the seats were small.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

Experience was good, the wifi hook up is somewhat tough

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

My luggage was damaged 1 wheel was out I can't find it nowhere

Took 3 hours to check in and drop off our suitcases. Half of the passengers were still in line by boarding time. The computer systems and staff were very slow. Staff were also disorganized and kept allowing later flights to skip lines. Suitcases were piling on that several other passengers didn't get their suitcases. Then, we were sitting in the plane for 2 hours and were told that the flight was overbooked. We missed our connecting flight and had to fly the following day but with a stop over. Good thing ONE WestJet customer rep was pleasant and actually knew how to do her job when we wanted to rebook to a direct flight. Thank you to Kim at Toronto airport. Terrible experience at PUJ. Won't go back to Dominican Republic.

Great seats, super comfortable, but no in flight entertainment which was a let down

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I when to Jamaica for my dad funeral and I did not get my luggage from westjet . I add to buy clothes putting me financial debt i did no want to be in Westjet did not call me to apologize are to inquire about my luggage I am still angry about it

Ground staff was not helpful, but staff at the business counter were excellent.

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

Overall a good experience as this leg I was in Business Class. The Lounge was amazing with a view of the planes. The flight attendant spoke way to quickly when giving the information for take off and landing and it would be of no use to a first time traveler. Overall a great airline to travel on.

I travelled in Business class for the first time and wish I could do that again.

The crew from Toronto Santiago (and the other way) weren't nice people. They seemed angry. Other flights with Air Canada had much nicer crews. Bathrooms always had sticky floors. Yuck!

No entertainment system. Paid extra for wider seats but not worth the cost. Flight left a little late and arrived early.

We boarded and then deboarded the plane after being told it needed something done that couldn't be fixed. Sent notice about 3h flight delay, then they clawed it back and we were 1h delayed. Very poor communication.

Was notified on a timely manner of any changes, if any, of the flight schedules.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

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

Information on your arrival and departure airports