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Cheap flights from Winnipeg to Simpson Bay from C$ 481

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Simpson Bay departing on 4/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Winnipeg to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:00 a.m. - 3:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
8h 21m1 stop Toronto Pearson Intl
WestJet Logo
4:20 p.m. - 11:35 a.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
21h 15m1 stop Toronto Pearson Intl
C$ 481WestJet
Fri, 4 Dec - Sun, 13 Dec
WestJet Logo
5:00 a.m. - 3:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
8h 21m1 stop Toronto Pearson Intl
WestJet Logo
4:20 p.m. - 10:50 p.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
32h 30m2 stops Toronto Pearson Intl Edmonton
C$ 496WestJet
Fri, 4 Dec - Sun, 13 Dec
WestJet Logo
12:55 p.m. - 3:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
48h 26m2 stops Edmonton Toronto Pearson Intl
WestJet Logo
4:20 p.m. - 10:50 p.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
56h 30m2 stops Toronto Pearson Intl Edmonton
C$ 509WestJet
Fri, 4 Dec - Sun, 13 Dec
WestJet Logo
6:45 a.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
30h 36m2 stops Edmonton Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:05 p.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
45h 45m2 stops Toronto Pearson Intl Edmonton
C$ 523WestJet
Mon, 26 Oct - Fri, 30 Oct
WestJet Logo
12:55 p.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
24h 26m2 stops Edmonton Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:45 a.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
10h 25m1 stop Toronto Pearson Intl
C$ 523WestJet
Mon, 26 Oct - Fri, 30 Oct
WestJet Logo
8:05 p.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
17h 16m1 stop Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:45 a.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
10h 25m1 stop Toronto Pearson Intl
C$ 523WestJet
Mon, 26 Oct - Fri, 30 Oct
WestJet Logo
8:05 p.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
17h 16m1 stop Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:45 a.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
10h 25m1 stop Toronto Pearson Intl
C$ 524WestJet
Mon, 26 Oct - Fri, 30 Oct
WestJet Logo
6:45 a.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
30h 36m2 stops Edmonton Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:05 p.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
45h 45m2 stops Toronto Pearson Intl Edmonton
C$ 524WestJet
Mon, 26 Oct - Fri, 30 Oct
WestJet Logo
12:55 p.m. - 2:21 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
24h 26m2 stops Edmonton Toronto Pearson Intl
WestJet Logo
3:20 p.m. - 12:45 a.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
10h 25m1 stop Toronto Pearson Intl
C$ 524WestJet
Mon, 26 Oct - Fri, 30 Oct
Multiple Airlines Logo
10:00 a.m. - 2:45 p.m.YWG  Winnipeg-SXM Simpson Bay Princess Juliana
26h 45m3 stops Toronto Pearson Intl Ottawa Montreal Pierre Elliott Trudeau Intl
Multiple Airlines Logo
4:20 p.m. - 10:50 p.m.SXM  Simpson Bay Princess Juliana-YWG Winnipeg
32h 30m2 stops Toronto Pearson Intl Edmonton
C$ 642Multiple Airlines
Fri, 4 Dec - Sun, 13 Dec

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WestJet flights from Winnipeg to Simpson Bay

Our best WestJet deals on Winnipeg to Simpson Bay flight tickets
WestJet
4 Dec
YWG5:00 a.m.Winnipeg
8h 21m
1 stop
SXM3:21 p.m.Simpson Bay Princess Juliana
13 Dec
SXM4:20 p.m.Simpson Bay Princess Juliana
21h 15m
1 stop
YWG11:35 a.m.Winnipeg
C$ 481
WestJet
4 Dec
YWG5:00 a.m.Winnipeg
8h 21m
1 stop
SXM3:21 p.m.Simpson Bay Princess Juliana
13 Dec
SXM4:20 p.m.Simpson Bay Princess Juliana
32h 30m
2 stops
YWG10:50 p.m.Winnipeg
C$ 496
WestJet
4 Dec
YWG12:55 p.m.Winnipeg
48h 26m
2 stops
SXM3:21 p.m.Simpson Bay Princess Juliana
13 Dec
SXM4:20 p.m.Simpson Bay Princess Juliana
56h 30m
2 stops
YWG10:50 p.m.Winnipeg
C$ 509

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 10 August 2026.
Use the filters below to find and compare flights from Winnipeg to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Fri 4/12

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

1 stop8h 21m

Simpson Bay Princess Juliana

Sun 13/12

4:20 p.m.-11:35 a.m.

1 stop21h 15m

C$ 481

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Fri 4/12

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

1 stop8h 21m

Simpson Bay Princess Juliana

Sun 13/12

4:20 p.m.-10:50 p.m.

2 stops32h 30m

C$ 496

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Fri 4/12

12:55 p.m.-3:21 p.m.

2 stops48h 26m

Simpson Bay Princess Juliana

Sun 13/12

4:20 p.m.-10:50 p.m.

2 stops56h 30m

C$ 509

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

6:45 a.m.-2:21 p.m.

2 stops30h 36m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:05 p.m.

2 stops45h 45m

C$ 523

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

12:55 p.m.-2:21 p.m.

2 stops24h 26m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:45 a.m.

1 stop10h 25m

C$ 523
Quickest round-trip

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

8:05 p.m.-2:21 p.m.

1 stop17h 16m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:45 a.m.

1 stop10h 25m

C$ 523

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

8:05 p.m.-2:21 p.m.

1 stop17h 16m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:45 a.m.

1 stop10h 25m

C$ 524

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

6:45 a.m.-2:21 p.m.

2 stops30h 36m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:05 p.m.

2 stops45h 45m

C$ 524

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

12:55 p.m.-2:21 p.m.

2 stops24h 26m

Simpson Bay Princess Juliana

Fri 30/10

3:20 p.m.-12:45 a.m.

1 stop10h 25m

C$ 524

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Fri 4/12

10:00 a.m.-2:45 p.m.

3 stops26h 45m

Simpson Bay Princess Juliana

Sun 13/12

4:20 p.m.-10:50 p.m.

2 stops32h 30m

C$ 642

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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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

Can stopping save me money on Winnipeg to Simpson Bay flights?

You could potentially save up to 27% on your flight if you consider stops on a Winnipeg to Simpson Bay flight.

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

Fastest flight time

26h 45m

Direct flights

None
The fastest flight from Winnipeg to Simpson Bay takes 26h 45m
There are no direct flights from Winnipeg to Simpson Bay. There are no popular flight routes from Winnipeg to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Winnipeg to Simpson Bay

  • 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 26h 45m.

  • 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?

  • 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?

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
WestJetPriceFrom C$ 600Free CancellationRating
7.2
3,430 reviews
Search WestJet flights

Travelling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
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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