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C$ 167+ Cheap flights to Simpson Bay

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.
— SXM
20 Feb — 27 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Simpson Bay in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Simpson Bay
Explore the most affordable flight options available to Simpson Bay. Find the lowest fares based on data from user searches, with prices last updated on 21 January 2026.

Tue 3/39:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
WestJet
Wed 11/33:20 p.m.
SXM
-
YYZ
Nonstop5h 22m
WestJet
Deal found 19/1C$ 420
Thu 22/12:45 p.m.
YYZ
-
SXM
2 stops22h 05m
United Airlines
Tue 27/12:52 p.m.
SXM
-
YYZ
2 stops24h 22m
United Airlines
Deal found 19/1C$ 426
Sat 31/17:40 p.m.
YYZ
-
SXM
1 stop17h 10m
United Airlines
Sat 7/22:40 p.m.
SXM
-
YYZ
1 stop10h 19m
United Airlines
Deal found 19/1C$ 433
Fri 27/25:30 p.m.
YYZ
-
SXM
1 stop21h 27m
United Airlines
Fri 6/34:55 p.m.
SXM
-
YYZ
1 stop7h 51m
United Airlines
Deal found 21/1C$ 438
Mon 2/39:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
Multiple Airlines
Wed 11/32:20 p.m.
SXM
-
YYZ
1 stop9h 00m
Multiple Airlines
Deal found 19/1C$ 448
Thu 30/48:30 a.m.
YYZ
-
SXM
Nonstop4h 44m
WestJet
Tue 5/52:10 p.m.
SXM
-
YYZ
Nonstop5h 00m
WestJet
Deal found 20/1C$ 451
Wed 25/29:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
Multiple Airlines
Wed 4/33:20 p.m.
SXM
-
YYZ
1 stop9h 00m
Multiple Airlines
Deal found 20/1C$ 452
Mon 23/29:30 a.m.
YYZ
-
SXM
Nonstop4h 47m
Multiple Airlines
Wed 4/33:20 p.m.
SXM
-
YYZ
1 stop9h 00m
Multiple Airlines
Deal found 20/1C$ 453
Fri 23/19:30 a.m.
YYZ
-
SXM
Nonstop4h 51m
WestJet
Mon 26/14:20 p.m.
SXM
-
YYZ
Nonstop5h 23m
WestJet
Deal found 20/1C$ 456
Mon 19/14:20 p.m.
YTZ
-
SXM
2 stops21h 20m
Air Canada
Thu 22/13:40 p.m.
SXM
-
YTZ
2 stops30h 48m
Air Canada
Deal found 18/1C$ 489
Tue 24/38:00 a.m.
YTZ
-
SXM
1 stop26h 55m
Air Transat
Mon 30/312:05 p.m.
SXM
-
YTZ
1 stop27h 00m
Air Transat
Deal found 19/1C$ 518
Thu 22/110:25 a.m.
YTZ
-
SXM
2 stops26h 25m
Air Canada
Tue 27/13:40 p.m.
SXM
-
YTZ
2 stops19h 02m
Air Canada
Deal found 19/1C$ 524

Find flight deals to Simpson Bay

Find the latest flights to Simpson Bay in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 21 January 2026.

Round-trip from

C$ 420

One-way from

C$ 167

Popular in

December

Cheapest in

June

Average price

C$ 644

Good round-trip deal

C$ 511 or less

Good one-way deal

C$ 273 or less
WestJet
  • WestJet
  • 3/3-11/3
  • Nonstop
  • 10h 09m total
  • Toronto to Simpson Bay
Search Deals
Air Transat
  • Air Transat
  • 31/3
  • 1 total stop
  • 19h 40m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Toronto to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a one-way flight from Toronto to Simpson Bay Princess Juliana.
Search Deals

Cheapflights Fare Finder

 
Locate flights to Simpson Bay that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 21 January 2026.
Use the filters below to find and compare flights to Simpson Bay that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 27/2

9:00 p.m.-3:57 p.m.

1 stop17h 57m

Simpson Bay Princess Juliana

Fri 6/3

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

1 stop7h 51m

C$ 442

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 2/3

7:30 a.m.-4:00 p.m.

1 stop7h 30m

Simpson Bay Princess Juliana

Tue 10/3

4:01 p.m.-10:17 a.m.

1 stop18h 16m

C$ 444

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 31/1

5:30 p.m.-3:51 p.m.

2 stops21h 21m

Simpson Bay Princess Juliana

Sat 7/2

5:00 p.m.-1:43 p.m.

2 stops21h 43m

C$ 445

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 22/2

9:30 a.m.-3:17 p.m.

Nonstop4h 47m

Simpson Bay Princess Juliana

Wed 4/3

3:20 p.m.-11:20 p.m.

1 stop9h 00m

C$ 467

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 17/4

1:00 p.m.-12:27 p.m.

2 stops23h 27m

Simpson Bay Princess Juliana

Thu 23/4

1:35 p.m.-3:46 p.m.

2 stops26h 11m

C$ 489

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 22/2

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

2 stops26h 50m

Simpson Bay Princess Juliana

Wed 4/3

2:52 p.m.-3:02 p.m.

3 stops25h 10m

C$ 491

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Wed 28/1

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

2 stops17h 10m

Simpson Bay Princess Juliana

Tue 10/2

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

2 stops24h 22m

C$ 491

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 2/3

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

2 stops17h 10m

Simpson Bay Princess Juliana

Sun 8/3

1:20 p.m.-2:20 p.m.

2 stops25h 00m

C$ 500

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Tue 24/3

10:00 a.m.-12:50 p.m.

1 stop26h 50m

Simpson Bay Princess Juliana

Sun 29/3

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

1 stop18h 14m

C$ 500

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Thu 26/2

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

2 stops39h 50m

Simpson Bay Princess Juliana

Wed 4/3

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

2 stops24h 22m

C$ 500

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/1

Showing 1-10 of 34 results
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Best time to book a flight to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 to Simpson Bay

When is the best time to book a flight 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 16 January 2026.

Booking 24 days in advance of your planned departure date is, on average, the best time to get cheap flights to Simpson Bay. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

How long is the flight to Simpson Bay?

On average, a flight from Toronto to Simpson Bay takes 9 hours 0 minutes. Flights to Simpson Bay from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

Weekly flight availability to Simpson Bay

The most flights from Toronto to Simpson Bay are scheduled on a Monday (2 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

What are the most popular airlines that fly to Simpson Bay?

The most popular airlines flying from Toronto to Simpson Bay are WestJet, Air Canada and Air Transat.

WestJet
WestJet
From C$ 400
Air Transat
Air Transat
From C$ 505
Air Canada
Air Canada
From C$ 368
United Airlines
United Airlines
From C$ 212

What are the cheapest airlines that fly to Simpson Bay?

The cheapest airlines flying from Toronto to Simpson Bay are United Airlines, American Airlines and Air Canada.

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 21 January 2026.
Read through reviews of airlines serving St. Maarten, such as Air Transat,United Airlines, andAmerican Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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
499 reviews
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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
9,191 reviews
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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
11,173 reviews
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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
3,247 reviews
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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
10,646 reviews
Air Transat
7.7
Good
499 reviews
Check prices

Boarding

7.9

Crew

8.4

Overall

7.7

Entertainment

7.0

Food

6.7

Comfort

7.3

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.

FAQs about flying to Simpson Bay

  • What airport do you fly into for flights to Simpson Bay?

    Booking a flight to Simpson Bay Princess Juliana (SXM) is your only option if you intend on flying to Simpson Bay. It is only a 0.9 km journey from Princess Juliana to Simpson Bay’s city centre. On average, Simpson Bay Princess Juliana has 1 flight from Toronto per day from 7 airlines.

  • Can I find cheaper flights to Simpson Bay if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Simpson Bay on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Simpson Bay?

    Based on reviews from Cheapflights users, United Airlines is rated the highest out of the airlines that fly to Simpson Bay.

  • What is the cheapest airport to fly to in Simpson Bay?

    Simpson Bay Princess Juliana is currently the cheapest airport to fly to in Simpson Bay. One-way flights to Simpson Bay Princess Juliana typically cost C$ 212, while round-trip flights cost around C$ 452.

  • How much is a round-trip flight to Simpson Bay?

    A round-trip flight to Simpson Bay will typically cost around C$ 607, however they can be found for as little as C$ 452.

  • Where does the fastest flight to Simpson Bay depart from?

    For those looking to save time traveling to Simpson Bay, Montreal offers the quickest one-way flight (4 hours 35 minutes).

  • Does Simpson Bay Princess Juliana have rental cars?

    Yes. Those touching down at Simpson Bay Princess Juliana can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Simpson Bay Princess Juliana?

    Yes. Simpson Bay Princess Juliana has hotels nearby for those requiring accommodations. Coco's Beach House Su is the closest property to Simpson Bay Princess Juliana (0.0 km away from Simpson Bay Princess Juliana).

See more FAQs

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Some of the lowest fares we’ve come across for flights to Simpson Bay.
Flights from Pearson Intl to Simpson Bay
Flights from Pierre Elliott Trudeau Intl to Simpson Bay

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How does Cheapflights help users find flights to Simpson Bay?

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Users can book flights with no change fees policies with our dedicated filters. Book flights to Simpson Bay flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights to Simpson Bay become cheaper?

Yes, Cheapflights offers price alerts on Simpson Bay flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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