SXM

C$ 221 Find Cheap Flights to Simpson Bay – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 461
Typical prices: C$ 561-C$ 948
United Airlines
Wed 5/12Wed 12/12
YYZ - SXM • 2 stops
Cheapest direct flights
C$ 478
Typical prices: C$ 549-C$ 943
Air Canada
Fri 7/12Sat 15/12
YYZ - SXM • Direct
Direct flights
You can fly direct with WestJet, Air Canada, and Air Transat. Average duration is 4h 52m
FAQs
FAQs
Top airlines
Most flights • 8 per week
Best reviews • 7.7 score
Airline reviews
+1
Airline reviews
+1
Top routes
Cheapest • 27% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 12 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
+1
Good to know
+1
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We hope you enjoy your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights to Simpson Bay

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Simpson Bay

Thu, 26 Nov - Sat, 12 Dec
United Airlines Logo
7:26 p.m. - 1:50 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
41h 24m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National
United Airlines Logo
5:00 p.m. - 2:25 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
22h 25m1 stop Washington, D.C. Dulles Intl
C$ 461United Airlines
Sat, 5 Dec - Sat, 12 Dec
United Airlines Logo
7:44 p.m. - 1:50 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
41h 06m2 stops Washington, D.C. Dulles Intl Newark
United Airlines Logo
5:00 p.m. - 2:25 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
22h 25m1 stop Washington, D.C. Dulles Intl
C$ 461United Airlines
Mon, 7 Dec - Tue, 15 Dec
Air Canada Logo
9:55 a.m. - 3:50 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
Air Canada Logo
4:50 p.m. - 9:10 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mdirect
C$ 478Air Canada
Tue, 8 Dec - Tue, 15 Dec
Air Canada Logo
9:55 a.m. - 3:50 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
Air Canada Logo
4:50 p.m. - 9:10 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mdirect
C$ 487Air Canada
Tue, 17 Nov - Tue, 24 Nov
American Airlines Logo
6:07 p.m. - 1:26 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
18h 19m1 stop Charlotte Douglas
American Airlines Logo
3:26 p.m. - 11:37 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
9h 11m1 stop Miami
C$ 509American Airlines
Sat, 28 Nov - Sat, 5 Dec
American Airlines Logo
6:00 a.m. - 2:10 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
7h 10m1 stop Philadelphia
American Airlines Logo
3:09 p.m. - 10:19 a.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
20h 10m1 stop Philadelphia
C$ 510American Airlines
Tue, 23 Feb - Tue, 2 Mar
Air Transat Logo
6:30 a.m. - 12:15 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mdirect
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 513Air Transat
Tue, 2 Mar - Tue, 9 Mar
Air Transat Logo
6:30 a.m. - 12:15 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mdirect
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 516Air Transat
Sat, 16 Jan - Sat, 30 Jan
WestJet Logo
6:35 a.m. - 12:30 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
WestJet Logo
1:30 p.m. - 5:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 519WestJet
Tue, 8 Dec - Tue, 15 Dec
WestJet Logo
6:45 a.m. - 3:25 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-SXM Simpson Bay Princess Juliana
7h 40m1 stop Toronto Pearson Intl
WestJet Logo
4:20 p.m. - 5:00 p.m.SXM  Simpson Bay Princess Juliana-YUL Montreal Pierre Elliott Trudeau Intl
25h 40m1 stop Toronto Pearson Intl
C$ 520WestJet
Booking Insights

Price, demand, and travel trends for flights to Simpson Bay

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Simpson Bay?

Toronto Pearson Intl Airport to Simpson Bay is the cheapest route at C$ 461 round-trip, found in the past 5 days on KAYAK. Montreal Pierre Elliott Trudeau Intl Airport to Simpson Bay is the most popular connection with round-trip deals from C$ 520.

How much is a flight to Simpson Bay?

On average, a round-trip flight from Canada to Simpson Bay costs C$ 704, based on KAYAK data over the past 12 months. Round-trip fares from Thunder Bay average C$ 624, while Toronto runs a bit higher at C$ 670.

What is the cheapest day to fly to Simpson Bay?

Tuesday is the cheapest day to fly to Simpson Bay at C$ 671 round-trip on average over the past 12 months on KAYAK. Friday is the most expensive at C$ 826.

What is the cheapest month to fly to Simpson Bay?

•June is the cheapest month to fly to Simpson Bay with an average price of C$ 593 round-trip.
•December (C$ 835) and February (C$ 797) are the most expensive.

Based on KAYAK data over the past 12 months.

What is the cheapest time of day to fly to Simpson Bay?

Morning flights to Simpson Bay are the cheapest at C$ 716 round-trip on average. Night flights are the most expensive at C$ 888.

What is a good deal for flights to Simpson Bay?

Flights under C$ 561 are considered a good deal. 25% of KAYAK users found round-trip flights to Simpson Bay at or below these prices, with the lowest fares from:
•Toronto C$ 527.

When are flights to Simpson Bay the cheapest?

Flights to Simpson Bay are cheapest 12 weeks before departure. Booking in this window typically costs about 25% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Simpson Bay

Low season

September

Cheapest flight

C$ 221
Beat the crowds with an average 62% drop in traveller numbers.
The most popular month to fly with an average 66% increase in traveller numbers.
One-way flight from Toronto Pearson Intl Airport to Simpson Bay

When to book flights to Simpson Bay

Are your dates flexible? Find out the best times to travel 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

Your questions about flights to Simpson Bay, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Simpson Bay is a good deal?

    A good deal on a flight to Simpson Bay is around C$ 561 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • How long are direct flights to Simpson Bay from different departure cities?

    Direct flight time to Simpson Bay varies depending on your departure city:

    • From Montreal: 4h 35m
    • From Toronto: 4h 45m

  • Which city has the cheapest flights to Simpson Bay?

    Based on fares booked in the past 5 days, the cheapest flights to Simpson Bay are from Toronto, starting at C$ 461 round-trip, and from Montreal, starting at C$ 520 round-trip.

  • How expensive are last-minute flights to Simpson Bay?

    Last-minute fares to Simpson Bay (booked within two weeks of departure) are typically 11% higher than the average round-trip fare of C$ 704.

  • What is the difference between the most popular and the most frequent airline at Simpson Bay?

    WestJet operates the most flights from Canada to Simpson Bay at 8 per week, while Air Canada is the airline most often selected by KAYAK users searching for flights from Canada to Simpson Bay. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airlines should I consider for flights to Simpson Bay?

  • How many flights serve Simpson Bay?

    Simpson Bay receives 2 flights per day and 17 per week from across the world. Toronto has the most flights to Simpson Bay, with 12 weekly flights.

Your guide to booking Simpson Bay flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Simpson Bay, book around 12 weeks before departure. Based on KAYAK data from the last 12 months, fares are historically about 25% lower during this window than last-minute fares.
  • For flights to Simpson Bay, a good round-trip fare is around C$ 561. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Simpson Bay in June. Round-trip fares historically average C$ 593, making June the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to morning to save up to C$ 172 per round-trip. Morning flights to Simpson Bay average C$ 716 compared to C$ 888 for evening flights.
  • Bag allowances vary by airline, fare type, cabin class, and route. On flights to Simpson Bay, some airlines may include bags at no extra cost. For example, Air Canada includes a carry-on bag and a checked bag in Economy Class, WestJet includes a carry-on bag and a checked bag in Economy Class, and Air Transat includes a carry-on bag and a checked bag in Economy Class. Always check the fare details before booking, since bag policies can change by ticket type.

Reviews of the top 5 airlines flying to Simpson Bay

 
Need help choosing which airline to fly with 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 584 reviews
7.0Entertainment
6.7Food
8.5Crew
7.9Boarding
7.3Comfort
Airline reviews

Very cold on aircraft. Everyone was wearing “Parker’s”to stay warm.

6.0 GoodGordon, Sep 2026
Read more Air Transat reviews

Very cold on aircraft. Everyone was wearing “Parker’s”to stay warm.

On one of the flights, the situation became sufficiently frustrating that a passenger openly expressed their dissatisfaction. Despite these complaints, we did not observe any meaningful improvement or receive an adequate explanation. The fact that members of our group experienced similar conditions on two separate aircraft is particularly concerning. We recognize that cabin temperatures may vary during a flight; however, the prolonged discomfort and the apparent lack of an effective response significantly affected our travel experience. Passengers reasonably expect a long-haul international flight to provide a tolerable cabin environment. When multiple passengers raise concerns about their comfort or well-being, those concerns should be acknowledged and addressed professionally.

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

The flight was terrible based off the temperature in the plane and the air smelled so stale and gross. I have never wanted to hosed lore in my life after I got off. The food was disgusting and seemingly low quality. The staff was friendly. The bathrooms were so gross after a couple of hours. I will definitely never book with them again.

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

I liked the reliability. I liked less the chair comfort...

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

They took us all the way to Monterrey to tell us they United were not allowed to land and we were sent back to Houston. Terrible experience.

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Very efficient. Economy is what economy is. Wish it had been direct. Excellent setup in Newark for commuters and access to charging stations and wifi Flight could’ve had free wifi

All good except waiting for gate for over an hour at Ohare Chicago as usual. People missed flights because of that

My flight was cancelled and United Airlines could not rebook or help. My whole trip was then cancelled and I could not go to the funeral I needed to get to.

Boarding was a complete mess. The whole system went down. People got wrong seat for the first half an hour.

The website check in was poor. Baggage fees were in US dollars but registered in Canadian dollars. The site would not accept my credit card. Scanning the passport was the worst. Someone from United needs to try the process. I’m not a novice with tech and I have to say this was a bad experience. Everything else was great.

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

Friendly crew, but we were delayed for more than an hour and had to change planes due to maintenance issues.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

The flights were on time and I appreciated that the cabin crew helped passengers with overhead luggage - finding space etc - despite not being paid. Apparently their wages don’t start until takeoff. This makes no sense whatsoever.

It is stupid to have to go to Atlanta in order to get to Rochester NY. I was up for 36 hours because who can sleep on an airplane. I'll next do tht again.

Always a pleasure to fly with WestJet. I am however frustrated about the rising costs. We have started to resort to Ultra Basic fares to afford but really missing the extra bag but too costly.

The crew were all helpful, kind, and effective. There could have been more space under the seats.

Bumped from my connected flight, we arrived earlier than scheduled and I was bumped 4.5 hours later. There was no reason, they said my time I wouldn’t have connected in time. I had 41 minutes. None of Westjet customer service in airport could figure out why me and my 5 year old were bumped from flight we booked. We had 10 minutes to get to next gate after we got off the plane, one lady mentioned that’s not enough time to get to next gate. I was there in 3 minutes. Was originally suppose to fly out at 6:50 pm And was re scheduled to 11:45pm.

Everything went well, smooth flight, arrived on time, no lost luggage!

Horrible, delayed 3 hours due to a mechanical issue where the plane is deemed unsafe so we had to deplane after an hour on the tarmac. No credit was given even though plenty of passengers missed their connecting flights and then the baggage claim info showed that no flight was being loaded on the carousel whilst the bags were being dropped, so no one knew if it was the right flight or not since the arrivals screen didn’t show anything.

I think I'd sum up my experiences on this flight (Edinburgh to Toronto) by saying that Boeing 737s are simply too small for long-haul, transatlantic flights. The crew were excellent, the food was pretty good and the in-flight Wifi was a bonus. But 7+ hours on a narrow bodied aircraft with a single aisle and no in-built entertainment system, is a tough stretch - queues for the few toilets on board were lengthy at times; plus whilst the crew were doing food/drink service the aisle is blocked. It encourages you to stay in your seat the entire time (not great for those who need to get up and move around regularly) and the legroom is tight anyway. If this was priced as uber-budget, you could perhaps argue that you're getting what you paid for......but it wasn't and the price we paid was pretty standard for such trips (around £500 pp). I'd therefore urge caution and check the aircraft that is being used if booking with Westjet for flights to Canada from smaller regional airports on the Western edge of Europe. They do operate Boeing 787s from London and other major European centres - but it seems that if travelling from Scotland/Ireland the 737 is the aircraft of choice.......

Terrible. I was charged $75 for a checked bag when I only had a carry on. The lady at the desk said she couldn’t refund me the money and that I had to call westjet. I called the next day and they said they couldn’t refund me because there is no way to prove I didn’t have a checked bag.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

Very happy with flight experience. Great crew; friendly and attentive.

they could have remembered to put my luggage on the flight, it's frustrating and disappointing to have your bag left behind. now i get to deal with sh** tomorrow. do i have faith that AC will be on top of this? no. the flight was fine, run of the mill AC flight pay up for top notch service.

People next my seat were friendly so I had a good time on board. The flight attendants were generally kind and nice. The foods were so so. I will take AC next time.

The boarding process was going smoothly until the manager Bharti Singh insisted I check my duffle bag that fits under my seat. I travel with the duffle for this very reason. I know for a fact it fits under the seat. She was rude and aggressive, I was charged a check bag fee. She reminded me that I purchased a “basic”ticket. I fly Air Canada more then ten times a year and have spent thousands of dollars on tickets with Air Canada. Once the boarding closed there were many empty overhead bins. The airplane was an old, with no entertainment. The flight attendants were not pleasant, no smiles, not even friendly with each other. Over-all, seemed miserable. I fly all the time and have never experienced a flight crew so unpleasant. This was the worst flight I’ve ever had. If I didn’t have to fly Air Canada I would not use them again.

flight was full and no chance of getting a better sit. other than that. it was ok.

The flight was packed solid which shouldn’t be a problem, but when you realize that if you are over 5’7” tall there is no room to do anything but sit uptight it changes the perspective. Especially when you are in a seat that doesn’t even recline. Those seats should warrant a discount really. It’s preposterous that you have yo pay an extra $60ish to get 10cm more leg room but have to pay the same price as everyone else when you have seemingly less leg room and can’t even put your seat back the wee bit everyone else can. Offer them at a discount on booking even. I know tons of travelling kids/young people who wouldn’t mind sitting like that for five hours if a nice discount was offered. The staff was lovely and the touchdown was stellar but the extreme close quarters is what has me pondering another means of travel whenever possible.

It was a good flight and we arrived on time, plane was clean.

$4 for headphones to use the multimedia system, games that are boring.....small oat bar as a snack....Porter has better snacks and entertainment

I didn't like that they wanted extra money to watch a movie on the other airlines it's free that I use anyway

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 like the professionalism, schedule was respected, All personnal helped me given I am hard hearing in planes

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I got bumped by Qantas to American Airlines incurring a 6 hr layover at lax. I was not happy

Air conditioning was out for about 15 minutes that made it uncomfortable. WiFi went out halfway into the flight. Flight was about 45 minutes late.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

Baggage allowances are terrible and the experience of only being allowed one bag and paying so much to take sporting equipment to a known ski area should be addressed.

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

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

Baggage claim took too long and priority bags were not delivered first.

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