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C$ 208+ Cheap flights from 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 3/11. 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.
SXM — YYZ
17 Oct — 24 Oct1
1 adult
1 adult, Economy

What to know about flights from Simpson Bay

Discover essential information about flights departing from Simpson Bay, including flight schedules, destinations, airlines operating at the Simpson Bay airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 17 September 2025.

Cheapest airline

Winair

Good round-trip deal

C$ 501 or less

Good one-way deal

C$ 276 or less
On average, Winair currently has the cheapest one-way flight from Simpson Bay Princess Juliana (avg. price of C$ 402).
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Price to beat on a round-trip flight from Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Simpson Bay Princess Juliana.
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Find flights from Simpson Bay

Cheapest flights from Simpson Bay
Explore the most affordable flight options available from Simpson Bay. Find the lowest fares based on data from user searches, with prices last updated on 17 September 2025.

Thu 30/101:52 p.m.SXM - YYZ
1 stop19h 44mUnited Airlines
Sat 8/115:30 p.m.YYZ - SXM
1 stop21h 27mUnited Airlines
Deal found 17/9C$ 381
Sat 1/111:20 p.m.SXM - YYZ
1 stop10h 39mUnited Airlines
Sat 8/115:30 p.m.YYZ - SXM
1 stop21h 27mUnited Airlines
Deal found 17/9C$ 387
Thu 6/114:20 p.m.SXM - YYZ
Nonstop5h 23mMultiple Airlines
Fri 14/119:00 p.m.YYZ - SXM
1 stop17h 57mMultiple Airlines
Deal found 17/9C$ 407
Thu 30/103:20 p.m.SXM - YYZ
Nonstop5h 23mMultiple Airlines
Sat 8/115:30 p.m.YYZ - SXM
1 stop21h 27mMultiple Airlines
Deal found 17/9C$ 418
Thu 6/114:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Fri 14/119:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Deal found 16/9C$ 420
Sat 27/91:35 p.m.SXM - YYZ
1 stop8h 48mUnited Airlines
Sun 2/115:50 a.m.YYZ - SXM
1 stop8h 07mUnited Airlines
Deal found 16/9C$ 440
Thu 13/114:20 p.m.SXM - YYZ
Nonstop5h 23mWestJet
Thu 27/119:30 a.m.YYZ - SXM
Nonstop4h 51mWestJet
Deal found 17/9C$ 443
Sat 1/114:00 p.m.SXM - YUL
1 stop24h 16mUnited Airlines
Sat 8/112:13 p.m.YUL - SXM
2 stops24h 44mUnited Airlines
Deal found 16/9C$ 516
Sat 1/114:24 p.m.SXM - YUL
2 stops20h 51mAmerican Airlines
Sat 8/112:29 p.m.YUL - SXM
1 stop22h 31mAmerican Airlines
Deal found 16/9C$ 581
Sun 7/124:20 p.m.SXM - YUL
1 stop9h 23mMultiple Airlines
Sun 14/128:50 a.m.YUL - SXM
2 stops30h 10mMultiple Airlines
Deal found 17/9C$ 589
Thu 30/104:24 p.m.SXM - YUL
2 stops17h 26mAmerican Airlines
Thu 6/114:00 p.m.YUL - SXM
2 stops20h 50mAmerican Airlines
Deal found 17/9C$ 590
Sat 1/1112:05 p.m.SXM - YUL
Nonstop5h 00mAir Transat
Sat 8/116:20 a.m.YUL - SXM
Nonstop4h 35mAir Transat
Deal found 16/9C$ 622

Find flights from Simpson Bay within your budget

 
Find flights departing from Simpson Bay that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 17 September 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Thu 6/11

4:20 p.m.-8:43 p.m.

Nonstop5h 23m

Toronto Pearson Intl

Fri 14/11

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

1 stop17h 57m

C$ 407

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Thu 30/10

1:52 p.m.-9:36 a.m.

1 stop19h 44m

Toronto Pearson Intl

Sat 8/11

3:45 p.m.-3:57 p.m.

2 stops23h 12m

C$ 418

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Sat 27/9

1:35 p.m.-10:23 p.m.

1 stop8h 48m

Toronto Pearson Intl

Sun 2/11

5:50 a.m.-2:57 p.m.

1 stop8h 07m

C$ 440

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Sat 27/9

1:35 p.m.-10:23 p.m.

1 stop8h 48m

Toronto Pearson Intl

Thu 30/10

7:40 p.m.-12:50 p.m.

2 stops17h 10m

C$ 446

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Sat 27/9

1:35 p.m.-10:04 a.m.

2 stops20h 29m

Toronto Pearson Intl

Sat 1/11

7:40 p.m.-3:57 p.m.

2 stops20h 17m

C$ 453

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Thu 30/10

1:52 p.m.-9:58 a.m.

2 stops20h 06m

Toronto Pearson Intl

Thu 6/11

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

2 stops39h 50m

C$ 457

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Sat 27/9

1:35 p.m.-10:23 p.m.

1 stop8h 48m

Toronto Pearson Intl

Wed 29/10

2:45 p.m.-12:50 p.m.

2 stops22h 05m

C$ 477

Simpson BayToronto

SXM - YYZ

SXMYYZ

Simpson Bay Princess Juliana

Thu 6/11

2:52 p.m.-9:36 a.m.

1 stop19h 44m

Toronto Pearson Intl

Fri 14/11

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

1 stop17h 57m

C$ 508

Simpson BayMontreal

SXM - YUL

SXMYUL

Simpson Bay Princess Juliana

Sat 1/11

4:00 p.m.-4:16 p.m.

1 stop24h 16m

Montreal Pierre Elliott Trudeau Intl

Sat 8/11

2:13 p.m.-3:57 p.m.

2 stops24h 44m

C$ 516

Simpson BayMontreal

SXM - YUL

SXMYUL

Simpson Bay Princess Juliana

Sat 1/11

4:24 p.m.-1:15 p.m.

2 stops20h 51m

Montreal Pierre Elliott Trudeau Intl

Sat 8/11

2:29 p.m.-2:00 p.m.

1 stop22h 31m

C$ 581

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 53 results
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Best time to book a flight from Simpson Bay

Have a flexible travel schedule? Discover the best time to fly from 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.

Travel insights for flights from Simpson Bay

Get recent, data-driven insights about flights from Simpson Bay including ideal travel times, pricing trends, and more.

Which airlines fly from Simpson Bay?

For flights departing from Simpson Bay check dates and pricing for the following: WestJet. This airline departs to the following popular destinations: Toronto.

WestJet
WestJet
From C$ 315
Winair
Winair
From C$ 243
American Airlines
American Airlines
From C$ 1,200

What are popular destinations to fly to from Simpson Bay?

From Simpson Bay you can expect to find greater availability for the following destinations: Gustavia (182 flights per day), Oranjestad (29 flights per day) and Saba Island (27 flights per day).

Toronto
Toronto
From C$ 236
Montreal
Montreal
From C$ 318
Washington, D.C.
Washington, D.C.
From C$ 181
Miami
Miami
From C$ 670

What is the cheapest place to fly to from Simpson Bay?

The cheapest city to fly to from Simpson Bay is Washington, D.C., with prices starting at C$ 249. Explore other affordable destinations below.

Washington, D.C.
Washington, D.C.
From C$ 181
Toronto
Toronto
From C$ 236
Montreal
Montreal
From C$ 318
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 319

Airline reviews for flights from Simpson Bay

Get insights into the airlines that provide service from 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 airline for your flight from Simpson Bay. In the last 7 days, Cheapflights users made a total of 629,999 searches.
Read through reviews of airlines serving Simpson Bay, such as WestJet. 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.
WestJet
7.2
Good
3,095 reviews
Check prices

Comfort

7.1

Boarding

7.4

Food

6.2

Crew

7.9

Entertainment

6.1

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Sugith,Jan 2025

CUN - YYZ

On time departure. Good service on board. Comfort Plus seating was comfortable.
WestJet
7.2
Good
3,095 reviews
WestJet
7.2
Good
3,095 reviews
Check prices

Comfort

7.1

Boarding

7.4

Food

6.2

Crew

7.9

Entertainment

6.1

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Sugith,Jan 2025

CUN - YYZ

On time departure. Good service on board. Comfort Plus seating was comfortable.

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Related info for your journey

Access useful and relevant information related to your journey from Simpson Bay. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 17 September 2025.

  • What are the most popular destinations to fly to from Simpson Bay?

    This month, the top selected destinations from Simpson Bay are Miami, New York John F Kennedy Intl Airport, Panama City. Throughout the year, Miami, Gustavia, New York are some of the top choices made by users flying from Simpson Bay.

  • What is the cheapest flight from Simpson Bay to anywhere?

    Users have flown out of Simpson Bay for as low as C$ 241 to Gustavia (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 733 to fly from Simpson Bay.

  • What are the cheapest airlines flying from Simpson Bay to anywhere?

    According to our data, users have found Winair, WestJet, and American Airlines to have the cheapest round-trip prices from Simpson Bay. Some of the destinations and prices are as follows: Winair flights from Simpson Bay to Road Town Beef Island (C$ 335). WestJet flights from Simpson Bay to Toronto (C$ 434). American Airlines flights from Simpson Bay to Bozeman Gallatin Field (C$ 1,651).

  • What is the cheapest first class flight from Simpson Bay?

    If you’re looking to fly first-class from Simpson Bay to anywhere, put Toronto on your list as prices start at C$ 2,134 for this destination.

  • How does Cheapflights help users find flights from Simpson Bay?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Simpson Bay today with Cheapflights!

  • Why should you use Cheapflights to find cheap flight tickets from Simpson Bay?

    Cheapflights simply makes it quick and affordable to book flights from Simpson Bay by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

  • Can Cheapflights find flights from Simpson Bay with no change fees?

    Need flexible booking options for your flight from Simpson Bay ? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

    Yes! Start tracking prices for flights from Simpson Bay today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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How does Cheapflights help users find flights from Simpson Bay?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Simpson Bay today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Simpson Bay?

Cheapflights simply makes it quick and affordable to book flights from Simpson Bay by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Simpson Bay with no change fees?

Need flexible booking options for your flight from Simpson Bay ? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

Yes! Start tracking prices for flights from Simpson Bay today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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