How long is the flight from Winnipeg to Simpson Bay?

Airlines like Air Canada and WestJet fly from Winnipeg to Simpson Bay in about 8h 25m. The time it takes to get you to your destination can typically vary by up to 05m. There are 4661 km between Winnipeg and Simpson Bay. This flight may include one or multiple stops.

What is the cheapest airline to fly from Winnipeg to Simpson Bay round-trip?

According to our current data, WestJet (C$ 603), offers the cheapest pricing from Winnipeg to Simpson Bay.

What is the cheapest time of day to fly from YWG to SXM?

When flying from Winnipeg to Simpson Bay, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Can I find deals for flights from Winnipeg to Simpson Bay that include hotel bookings?

Yes. In addition to deals on Winnipeg to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Winnipeg to Simpson Bay?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Simpson Bay.

Can I find deals for business class flights from Winnipeg to Simpson Bay?

Yes. Cheapflights offers flight deals from Winnipeg to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

C$ 314+ Cheap Flights from Winnipeg to Simpson Bay

Cheap flight deals from Winnipeg to Simpson Bay

Enter your travel dates to find the best prices.

Cheapest

Best

Last-minute

One-way

Cheapest flights from Winnipeg to Simpson Bay
Explore the most affordable flight options available from Winnipeg to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 October 2026.

Mon 30/116:15 a.m. -

1 stop8h 30m

Fri 4/124:45 p.m. -

1 stop23h 24m

Deal found 20/10C$ 549

Thu 10/126:00 a.m. -

1 stop8h 25m

Thu 17/124:20 p.m. -

1 stop10h 24m

Deal found 22/10C$ 604

Thu 10/128:20 p.m. -

2 stops41h 25m

Thu 17/124:20 p.m. -

1 stop20h 45m

Deal found 22/10C$ 758

Find flight deals from Winnipeg to Simpson Bay

Round-trip from	C$ 549
One-way from	C$ 307

Air Canada
30/11-4/12
2 total stops
31h 54m total
Winnipeg to Simpson Bay

Search Deals

Air Canada
3/12-31/12
1 total stop
17h 50m total
Winnipeg to Simpson Bay

Search Deals

Cheapflights Fare Finder

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

Mon 22/2

9:05 a.m.-2:45 p.m.

1 stop28h 40m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 314

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Thu 7/1

7:00 a.m.-3:45 p.m.

2 stops31h 45m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 330

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 22/2

11:00 a.m.-2:45 p.m.

3 stops26h 45m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 485

Quickest round-trip

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Thu 10/12

6:00 a.m.-3:25 p.m.

1 stop8h 25m

Simpson Bay Princess Juliana

Thu 17/12

4:20 p.m.-1:44 a.m.

1 stop10h 24m

C$ 604

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 30/11

6:15 a.m.-3:45 p.m.

1 stop8h 30m

Simpson Bay Princess Juliana

Fri 4/12

4:45 p.m.-7:25 p.m.

2 stops27h 40m

C$ 608

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 1/2

9:05 a.m.-2:45 p.m.

1 stop28h 40m

Simpson Bay Princess Juliana

Fri 12/2

4:45 p.m.-2:49 p.m.

1 stop23h 04m

C$ 711

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Sorted by cheapest first

Best time to book a flight from Winnipeg to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Winnipeg with our price prediction graph.

YWG-SXM

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.

Reviews of airlines servicing Simpson Bay

Check out reviews from past customers who have flown with WestJet from Winnipeg to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

WestJet

7.2

Good

3,445 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

WestJet

7.2

Good

3,445 reviews

WestJet

7.2

Good

3,445 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

Related info for your journey

How long is the flight from Winnipeg to Simpson Bay?
Airlines like Air Canada and WestJet fly from Winnipeg to Simpson Bay in about 8h 25m. The time it takes to get you to your destination can typically vary by up to 05m. There are 4661 km between Winnipeg and Simpson Bay. This flight may include one or multiple stops.
What is the cheapest airline to fly from Winnipeg to Simpson Bay round-trip?
According to our current data, WestJet (C$ 603), offers the cheapest pricing from Winnipeg to Simpson Bay.
Can I find deals for flights from Winnipeg to Simpson Bay that include hotel bookings?
Yes. In addition to deals on Winnipeg to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Winnipeg to Simpson Bay?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Simpson Bay.
Can I find deals for business class flights from Winnipeg to Simpson Bay?
Yes. Cheapflights offers flight deals from Winnipeg to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Simpson Bay Princess Juliana Airport car rentals

Philipsburg car rentals

Top airline flying from Winnipeg to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 609	AverageC$ 900	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

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How does Cheapflights help users find flights from Winnipeg to Simpson Bay?

Cheapflights makes it easy to find Winnipeg to Simpson Bay flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

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

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Simpson Bay, users can toggle the no change fees filter when performing a flight search.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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Cheap flights from Winnipeg to Simpson Bay from C$ 314

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 22/2. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Winnipeg to Simpson Bay

Cheapest flights from Winnipeg to Simpson BayExplore the most affordable flight options available from Winnipeg to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 October 2026.

Explore the most affordable flight options available from Winnipeg to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 October 2026.

Best flights from Winnipeg to Simpson BayDiscover carefully curated flight deals from Winnipeg to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 24 October 2026.

Discover carefully curated flight deals from Winnipeg to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 24 October 2026.

Last-minute flights from Winnipeg to Simpson BayDiscover last-minute flight deals from Winnipeg to Simpson Bay. Data last updated 24 October 2026 and is based on user searches.

Discover last-minute flight deals from Winnipeg to Simpson Bay. Data last updated 24 October 2026 and is based on user searches.

One-way flights from Winnipeg to Simpson BaySearch for one-way flight options from Winnipeg to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated 24 October 2026.

Search for one-way flight options from Winnipeg to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated 24 October 2026.

Find flight deals from Winnipeg to Simpson Bay

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One-way from

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Simpson Bay that are best for you.

Best time to book a flight from Winnipeg to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Winnipeg with our price prediction graph.

Reviews of airlines servicing Simpson Bay

Check out reviews from past customers who have flown with WestJet from Winnipeg to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

How long is the flight from Winnipeg to Simpson Bay?

What is the cheapest airline to fly from Winnipeg to Simpson Bay round-trip?

Can I find deals for flights from Winnipeg to Simpson Bay that include hotel bookings?

How can I find direct flights from Winnipeg to Simpson Bay?

Can I find deals for business class flights from Winnipeg to Simpson Bay?

Travelling to a place near Simpson Bay?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Winnipeg to Simpson Bay by cabin class

Find flights from Winnipeg to Simpson Bay, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Winnipeg and Simpson Bay flights

Browse other Winnipeg and Simpson Bay flight options. Last updated on 24 October 2026.

Other flights from Winnipeg

Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 24 October 2026.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Other flights to Simpson Bay

Explore flights to Simpson Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 24 October 2026.

Top airline flying from Winnipeg to Simpson Bay

Fly with Cheapflights

How does Cheapflights help users find flights from Winnipeg to Simpson Bay?

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

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

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

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Travel Smart

Cheapest flights from Winnipeg to Simpson Bay
Explore the most affordable flight options available from Winnipeg to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 October 2026.

Best flights from Winnipeg to Simpson Bay
Discover carefully curated flight deals from Winnipeg to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 24 October 2026.

Last-minute flights from Winnipeg to Simpson Bay
Discover last-minute flight deals from Winnipeg to Simpson Bay. Data last updated 24 October 2026 and is based on user searches.

One-way flights from Winnipeg to Simpson Bay
Search for one-way flight options from Winnipeg to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated 24 October 2026.