What is the cheapest airline that flies from Winnipeg to Simpson Bay Princess Juliana?

WestJet is the most popular carrier operating from Winnipeg to Simpson Bay Princess Juliana

When did momondo last update prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport are updated daily.

How many operators does momondo search for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

There is 1 operator available for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport as of July 2025.

How old do you have to be to fly from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 316 Cheap Flights from Winnipeg to Simpson Bay in 2025

1 adult

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Find the cheapest flights from Winnipeg to Simpson Bay

Round-trip

One-way

Cheap round-trip flights

8:05 p.m. - 3:21 p.m.YWG-SXM

17h 16m1 stop

4:20 p.m. - 12:35 a.m.SXM-YWG

10h 15m1 stop

C$ 727WestJet

Find Deal

Thu, 22 Jan - Tue, 3 Feb

6:15 a.m. - 3:21 p.m.YWG-SXM

31h 06m2 stops

4:20 p.m. - 12:39 a.m.SXM-YWG

10h 19m1 stop

C$ 742WestJet

Find Deal

Sat, 24 Jan - Tue, 3 Feb

11:05 a.m. - 4:00 p.m.YWG-SXM

26h 55m1 stop

3:40 p.m. - 4:35 p.m.SXM-YWG

26h 55m1 stop

C$ 745Air Canada

Find Deal

Mon, 26 Jan - Thu, 5 Feb

11:05 a.m. - 4:00 p.m.YWG-SXM

26h 55m1 stop

5:00 p.m. - 9:44 p.m.SXM-YWG

30h 44m1 stop

C$ 754Air Canada

Find Deal

Mon, 26 Jan - Wed, 4 Feb

8:05 p.m. - 3:21 p.m.YWG-SXM

17h 16m1 stop

4:20 p.m. - 11:32 a.m.SXM-YWG

21h 12m1 stop

C$ 757WestJet

Find Deal

Thu, 22 Jan - Sun, 1 Feb

5:38 p.m. - 12:15 p.m.YWG-SXM

16h 37m2 stops

1:45 p.m. - 11:43 a.m.SXM-YWG

23h 58m2 stops

C$ 905Delta

Find Deal

Fri, 23 Jan - Mon, 2 Feb

5:00 a.m. - 3:21 p.m.YWG-SXM

8h 21m1 stop

10:20 a.m. - 12:42 a.m.SXM-YWG

16h 22m3 stops

C$ 913

Find Deal

Tue, 4 Nov - Wed, 5 Nov

7:30 a.m. - 2:55 p.m.YWG-SXM

29h 25m1 stop

1:45 p.m. - 10:08 a.m.SXM-YWG

46h 23m2 stops

C$ 1,881Delta

Find Deal

Sun, 28 Dec - Fri, 2 Jan

2:15 p.m. - 1:50 p.m.YWG-SXM

21h 35m2 stops

4:55 p.m. - 8:48 p.m.SXM-YWG

29h 53m2 stops

C$ 1,935United Airlines

Find Deal

Sun, 28 Dec - Fri, 2 Jan

7:50 a.m. - 3:21 p.m.YWG-SXM

29h 31m2 stops

11:35 a.m. - 12:42 a.m.SXM-YWG

39h 07m3 stops

C$ 2,494

Find Deal

Sun, 28 Dec - Fri, 2 Jan

Delta flights from Winnipeg to Simpson Bay

Our best Delta deals on Winnipeg to Simpson Bay flight tickets

Delta

23 Jan

YWG5:38 p.m.Winnipeg

16h 37m

2 stops

SXM12:15 p.m.Simpson Bay Princess Juliana

2 Feb

SXM1:45 p.m.Simpson Bay Princess Juliana

23h 58m

2 stops

YWG11:43 a.m.Winnipeg

C$ 905

Find similar

Delta

28 Dec

YWG7:30 a.m.Winnipeg

29h 25m

1 stop

SXM2:55 p.m.Simpson Bay Princess Juliana

2 Jan

SXM1:45 p.m.Simpson Bay Princess Juliana

46h 23m

2 stops

YWG10:08 a.m.Winnipeg

C$ 1,881

Find similar

Delta

28 Dec

YWG5:00 a.m.Winnipeg

31h 55m

2 stops

SXM2:55 p.m.Simpson Bay Princess Juliana

2 Jan

SXM1:45 p.m.Simpson Bay Princess Juliana

46h 23m

2 stops

YWG10:08 a.m.Winnipeg

C$ 1,914

Find similar

WestJet flights from Winnipeg to Simpson Bay

Our best WestJet deals on Winnipeg to Simpson Bay flight tickets

WestJet

22 Jan

YWG8:05 p.m.Winnipeg

17h 16m

1 stop

SXM3:21 p.m.Simpson Bay Princess Juliana

3 Feb

SXM4:20 p.m.Simpson Bay Princess Juliana

10h 15m

1 stop

YWG12:35 a.m.Winnipeg

C$ 727

Find similar

WestJet

24 Jan

YWG6:15 a.m.Winnipeg

31h 06m

2 stops

SXM3:21 p.m.Simpson Bay Princess Juliana

3 Feb

SXM4:20 p.m.Simpson Bay Princess Juliana

10h 19m

1 stop

YWG12:39 a.m.Winnipeg

C$ 742

Find similar

WestJet

22 Jan

YWG8:05 p.m.Winnipeg

17h 16m

1 stop

SXM3:21 p.m.Simpson Bay Princess Juliana

1 Feb

SXM4:20 p.m.Simpson Bay Princess Juliana

21h 12m

1 stop

YWG11:32 a.m.Winnipeg

C$ 757

Find similar

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 22/1

8:05 p.m.-3:21 p.m.

1 stop17h 16m

Simpson Bay Princess Juliana

Tue 3/2

4:20 p.m.-12:35 a.m.

1 stop10h 15m

C$ 727

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 24/1

6:15 a.m.-3:21 p.m.

2 stops31h 06m

Simpson Bay Princess Juliana

Tue 3/2

4:20 p.m.-12:39 a.m.

1 stop10h 19m

C$ 742

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 26/1

11:05 a.m.-4:00 p.m.

1 stop26h 55m

Simpson Bay Princess Juliana

Thu 5/2

3:40 p.m.-4:35 p.m.

1 stop26h 55m

C$ 745

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 26/1

11:05 a.m.-4:00 p.m.

1 stop26h 55m

Simpson Bay Princess Juliana

Wed 4/2

5:00 p.m.-9:44 p.m.

1 stop30h 44m

C$ 754

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 22/1

8:05 p.m.-3:21 p.m.

1 stop17h 16m

Simpson Bay Princess Juliana

Sun 1/2

4:20 p.m.-11:32 a.m.

1 stop21h 12m

C$ 757

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 23/1

5:38 p.m.-12:15 p.m.

2 stops16h 37m

Simpson Bay Princess Juliana

Mon 2/2

1:45 p.m.-11:43 a.m.

2 stops23h 58m

C$ 905

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 4/11

5:00 a.m.-3:21 p.m.

1 stop8h 21m

Simpson Bay Princess Juliana

Wed 5/11

10:20 a.m.-12:42 a.m.

3 stops16h 22m

C$ 913

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:30 a.m.-2:55 p.m.

1 stop29h 25m

Simpson Bay Princess Juliana

Fri 2/1

1:45 p.m.-10:08 a.m.

2 stops46h 23m

C$ 1,881

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

2:15 p.m.-1:50 p.m.

2 stops21h 35m

Simpson Bay Princess Juliana

Fri 2/1

4:55 p.m.-8:48 p.m.

2 stops29h 53m

C$ 1,935

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:50 a.m.-3:21 p.m.

2 stops29h 31m

Simpson Bay Princess Juliana

Fri 2/1

11:35 a.m.-12:42 a.m.

3 stops39h 07m

C$ 2,494

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first

How to get the cheapest flight ticket from Winnipeg to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Simpson Bay?

The cheapest day to depart on your flight to Simpson Bay is on a Thursday when prices can be found for as low as C$ 759. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 1,476.

What is the cheapest time of day to depart on your flight to Simpson Bay?

Flying to Simpson Bay from Winnipeg in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as C$ 663 when looking at flights departing in the afternoon. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around C$ 1,177.

When to book flights from Winnipeg to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Winnipeg to Simpson Bay (YWG to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Simpson Bay

Best price found	C$ 316
Fastest flight time	8h 21m
Direct flights	None
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Winnipeg in the past 72 hours is C$ 316. The best round-trip flight deal from Winnipeg to Simpson Bay found on momondo in the last 72 hours is C$ 727.

The fastest flight from Winnipeg to Simpson Bay takes 8h 21m

There are no direct flights from Winnipeg to Simpson Bay. Popular non-direct route for this connection is Winnipeg Airport - Simpson Bay Princess Juliana Airport.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

Search flight deals

How far is Winnipeg to Simpson Bay Princess Juliana by plane?
There are 4653.2 km between Winnipeg and Simpson Bay Princess Juliana. In terms of flight time, this usually takes a little over 8h 21m.
When did momondo last update prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport are updated daily.
How many operators does momondo search for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?
There is 1 operator available for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport as of July 2025.
How old do you have to be to fly from Winnipeg Airport to Simpson Bay Princess Juliana Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Winnipeg to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Winnipeg to Simpson Bay is WestJet (100% of total bookings).

Best airlines flying from Winnipeg to Simpson Bay

Compare and see reviews for airlines that fly from Winnipeg to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 565	Free Cancellation	Rating 7.2 2,978 reviews		Search WestJet flights

Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Simpson Bay?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Simpson Bay. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to Simpson Bay with flexible booking policies on momondo?

Yes. All flights to Simpson Bay from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to Simpson Bay?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Simpson Bay from Winnipeg.

I’m not ready to book a flight from Winnipeg to Simpson Bay right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Winnipeg to Simpson Bay flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Winnipeg to Simpson Bay from C$ 316

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Simpson Bay departing on 13/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

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Filter for what you want

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Cheap round-trip flights

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Delta flights from Winnipeg to Simpson Bay

Our best Delta deals on Winnipeg to Simpson Bay flight tickets

WestJet flights from Winnipeg to Simpson Bay

Our best WestJet deals on Winnipeg to Simpson Bay flight tickets

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How to get the cheapest flight ticket from Winnipeg to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest time of day to depart on your flight to Simpson Bay?

What is the cheapest airline that flies from Winnipeg to Simpson Bay Princess Juliana?

WestJet is the most popular carrier operating from Winnipeg to Simpson Bay Princess Juliana

When to book flights from Winnipeg to Simpson Bay

Cheap Winnipeg to Simpson Bay (YWG to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Simpson Bay

Best price found

Fastest flight time

Direct flights

Airports in Simpson Bay

How far is Winnipeg to Simpson Bay Princess Juliana by plane?

When did momondo last update prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular airline from Winnipeg to Simpson Bay?

Best airlines flying from Winnipeg to Simpson Bay

Compare and see reviews for airlines that fly from Winnipeg to Simpson Bay with momondo

Travelling to a place near Simpson Bay?

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Simpson Bay?

Can I find flights from Winnipeg to Simpson Bay with flexible booking policies on momondo?

How can momondo help me find flights from Winnipeg to Simpson Bay?

I’m not ready to book a flight from Winnipeg to Simpson Bay right now. Can momondo alert me if prices change?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favourite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo