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Cheap flights from Winnipeg to Simpson Bay from C$ 306

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 26/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Winnipeg to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 11 September 2025.

Round-trip from

C$ 1,231

One-way from

C$ 306
Delta
  • Delta
  • 28/12-6/1
  • 4 total stops
  • 45h 28m total
  • Winnipeg to Simpson Bay
Search Deals
Air Canada
  • Air Canada
  • 26/10
  • 2 total stops
  • 40h 45m total
  • Winnipeg to Simpson Bay
Search Deals

Find flight deals from Winnipeg to Simpson Bay

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 11 September 2025.

Sun 28/125:56 p.m.YWG - SXM
2 stops18h 54mDelta
Tue 6/14:26 p.m.SXM - YWG
2 stops26h 34mDelta
Deal found 10/9C$ 1,231
Sun 28/128:05 p.m.YWG - SXM
1 stop17h 16mWestJet
Tue 6/14:20 p.m.SXM - YWG
1 stop10h 15mWestJet
Deal found 10/9C$ 1,337
Sun 28/128:40 a.m.YWG - SXM
2 stops27h 10mUnited Airlines
Fri 2/14:55 p.m.SXM - YWG
2 stops29h 56mUnited Airlines
Deal found 10/9C$ 1,734
Sun 28/127:30 a.m.YWG - SXM
1 stop29h 20mDelta
Fri 2/11:50 p.m.SXM - YWG
2 stops29h 16mDelta
Deal found 11/9C$ 2,102
Sun 28/128:05 p.m.YWG - SXM
1 stop17h 16mWestJet
Fri 2/14:20 p.m.SXM - YWG
1 stop10h 15mWestJet
Deal found 11/9C$ 2,110

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 11 September 2025.
Use the filters below to find and compare flights from Winnipeg to Simpson Bay that are best for you.

Fly from

Winnipeg

Fly to

Simpson Bay

Route

Depart

Return

Price

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

5:56 p.m.-2:50 p.m.

2 stops18h 54m

Simpson Bay Princess Juliana

Tue 6/1

4:26 p.m.-5:00 p.m.

2 stops26h 34m

C$ 1,231

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

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

1 stop17h 16m

Simpson Bay Princess Juliana

Tue 6/1

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

1 stop10h 15m

C$ 1,337

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

8:40 a.m.-1:50 p.m.

2 stops27h 10m

Simpson Bay Princess Juliana

Fri 2/1

4:55 p.m.-8:51 p.m.

2 stops29h 56m

C$ 1,734

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:30 a.m.-2:50 p.m.

1 stop29h 20m

Simpson Bay Princess Juliana

Fri 2/1

1:50 p.m.-5:06 p.m.

2 stops29h 16m

C$ 2,102

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

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

1 stop17h 16m

Simpson Bay Princess Juliana

Fri 2/1

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

1 stop10h 15m

C$ 2,110

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 26/10

7:05 p.m.-12:50 p.m.

2 stops40h 45m

C$ 306

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 26/10

7:30 a.m.-2:00 p.m.

3 stops29h 30m

C$ 396

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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.
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

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 11 September 2025.
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
3,091 reviews
Check prices

Food

6.2

Boarding

7.4

Overall

7.2

Entertainment

6.1

Crew

7.9

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
WestJet
7.2
Good
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Food

6.2

Boarding

7.4

Overall

7.2

Entertainment

6.1

Crew

7.9

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Winnipeg to Simpson Bay?

    Airlines like Delta, WestJet, and United Airlines fly from Winnipeg to Simpson Bay in about 17h 16m. The time it takes to get you to your destination can typically vary by up to 9h 54m. 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$ 566), 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.

  • What is the cheapest month to book a flight from Winnipeg to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Simpson Bay (average of C$ 324). Flying from Winnipeg to Simpson Bay in February is currently the most expensive (average of C$ 586). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

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

Top airline flying from Winnipeg to Simpson Bay

Discover the top airline that operate flights from Winnipeg to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 566AverageC$ 774FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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