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C$ 183+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
— SXM
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

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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 28 October 2025.

Sun 14/127:14 p.m.YYZ - SXM
1 stop17h 38mAmerican Airlines
Fri 19/123:10 p.m.SXM - YYZ
1 stop20h 06mAmerican Airlines
Deal found 27/10C$ 480
Sat 29/116:50 a.m.YYZ - SXM
1 stop8h 07mUnited Airlines
Sat 6/122:40 p.m.SXM - YYZ
1 stop20h 18mUnited Airlines
Deal found 27/10C$ 481
Tue 25/117:14 p.m.YYZ - SXM
2 stops20h 08mAmerican Airlines
Thu 4/122:51 p.m.SXM - YYZ
1 stop21h 21mAmerican Airlines
Deal found 25/10C$ 483
Sat 1/113:45 p.m.YYZ - SXM
2 stops24h 12mUnited Airlines
Sat 8/115:00 p.m.SXM - YYZ
2 stops19h 48mUnited Airlines
Deal found 26/10C$ 488
Fri 14/1111:59 a.m.YYZ - SXM
1 stop23h 03mAmerican Airlines
Thu 20/115:24 p.m.SXM - YYZ
2 stops17h 25mAmerican Airlines
Deal found 27/10C$ 490
Fri 12/127:40 p.m.YYZ - SXM
2 stops19h 17mUnited Airlines
Sat 20/122:40 p.m.SXM - YYZ
1 stop10h 19mUnited Airlines
Deal found 27/10C$ 491
Sun 2/119:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Tue 11/114:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Deal found 28/10C$ 501
Sun 9/119:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Fri 14/114:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Deal found 27/10C$ 504
Sun 2/117:14 p.m.YYZ - SXM
1 stop17h 36mAmerican Airlines
Thu 6/113:20 p.m.SXM - YYZ
1 stop9h 34mAmerican Airlines
Deal found 25/10C$ 505
Wed 10/124:30 p.m.YTZ - SXM
1 stop18h 25mAir Transat
Mon 15/121:05 p.m.SXM - YTZ
1 stop29h 20mAir Transat
Deal found 26/10C$ 513
Sat 6/123:30 p.m.YTZ - SXM
2 stops20h 48mAir Canada
Sat 13/123:40 p.m.SXM - YTZ
1 stop17h 30mAir Canada
Deal found 26/10C$ 579
Fri 14/1110:25 a.m.YTZ - SXM
2 stops26h 10mAir Canada
Thu 20/113:40 p.m.SXM - YTZ
1 stop21h 15mAir Canada
Deal found 27/10C$ 601

Flights to Simpson Bay in 2025

Find the latest flights to Simpson Bay in 2025, 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 28 October 2025.

Round-trip from

C$ 474

One-way from

C$ 189

Popular in

December

Cheapest in

October

Average price

C$ 569

Good round-trip deal

C$ 591 or less

Good one-way deal

C$ 327 or less
United Airlines
  • United Airlines
  • 26/1-3/2
  • 4 total stops
  • 51h 04m total
  • Toronto to Simpson Bay
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United Airlines
  • United Airlines
  • 1/11
  • 2 total stops
  • 33h 47m total
  • Toronto to Simpson Bay
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Toronto to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Toronto to Simpson Bay Princess Juliana.
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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 28 October 2025.
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

Sat 29/11

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

1 stop8h 07m

Simpson Bay Princess Juliana

Sat 6/12

5:00 p.m.-9:58 a.m.

2 stops17h 58m

C$ 481

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/2

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

2 stops17h 10m

Simpson Bay Princess Juliana

Thu 12/2

2:52 p.m.-9:58 a.m.

2 stops20h 06m

C$ 483

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Mon 2/2

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

2 stops17h 10m

Simpson Bay Princess Juliana

Thu 12/2

2:52 p.m.-9:58 a.m.

2 stops20h 06m

C$ 483

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 1/2

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

2 stops17h 10m

Simpson Bay Princess Juliana

Wed 11/2

2:52 p.m.-2:01 p.m.

2 stops24h 09m

C$ 483

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Fri 12/12

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

1 stop17h 57m

Simpson Bay Princess Juliana

Sat 20/12

2:40 p.m.-11:59 p.m.

1 stop10h 19m

C$ 485

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sat 31/1

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

1 stop17h 10m

Simpson Bay Princess Juliana

Sat 7/2

2:40 p.m.-11:54 p.m.

1 stop10h 14m

C$ 490

TorontoSimpson Bay

YYZ - SXM

YYZSXM

Toronto Pearson Intl

Sun 18/1

7:30 a.m.-3:51 p.m.

1 stop7h 21m

Simpson Bay Princess Juliana

Wed 28/1

2:52 p.m.-9:58 a.m.

2 stops20h 06m

C$ 501

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Wed 10/12

4:30 p.m.-11:55 a.m.

1 stop18h 25m

Simpson Bay Princess Juliana

Mon 15/12

1:05 p.m.-5:25 p.m.

1 stop29h 20m

C$ 513

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Tue 20/1

7:50 p.m.-11:55 a.m.

1 stop15h 05m

Simpson Bay Princess Juliana

Mon 26/1

1:05 p.m.-5:25 p.m.

1 stop29h 20m

C$ 580

TorontoSimpson Bay

YTZ - SXM

YTZSXM

Toronto Island

Fri 14/11

10:25 a.m.-1:35 p.m.

2 stops26h 10m

Simpson Bay Princess Juliana

Thu 20/11

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

1 stop21h 15m

C$ 601

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 35 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 24 October 2025.

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 5 hours 42 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.

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$ 435
Air Transat
Air Transat
From C$ 481
Air Canada
Air Canada
From C$ 474
United Airlines
United Airlines
From C$ 260

What are the cheapest airlines that fly to Simpson Bay?

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

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 28 October 2025.
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
7.8
Good
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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
469 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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
11,034 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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
3,148 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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
10,370 reviews
Air Transat
7.8
Good
469 reviews
Check prices

Boarding

7.9

Comfort

7.4

Crew

8.5

Entertainment

7.1

Food

6.8

Overall

7.8

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.

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.

  • 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$ 230, while round-trip flights cost around C$ 458.

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

    A round-trip flight to Simpson Bay will typically cost around C$ 691, however they can be found for as little as C$ 458.

  • 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. Simpson Bay Ocean View - Deluxe 1 Bedroom Condo! 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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Flights from Pearson Intl to Simpson Bay
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Flights from Pierre Elliott Trudeau Intl to Simpson Bay

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