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Cheap flights from Winnipeg to Simpson Bay from C$ 268

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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
27 Aug — 3 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Simpson Bay

Enter your travel dates to find the best prices.

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 28 July 2026.

Sat 12/95:00 a.m.
YWG
-
SXM
1 stop11h 00m
Air Canada
Sat 26/96:00 p.m.
SXM
-
YWG
1 stop18h 12m
Air Canada
Deal found 25/7C$ 557
Sat 5/97:00 a.m.
YWG
-
SXM
2 stops30h 20m
WestJet
Sun 13/93:20 p.m.
SXM
-
YWG
2 stops51h 50m
WestJet
Deal found 27/7C$ 593
Fri 4/97:45 p.m.
YWG
-
SXM
1 stop20h 15m
Air Canada
Sat 12/96:00 p.m.
SXM
-
YWG
1 stop18h 12m
Air Canada
Deal found 27/7C$ 605
Fri 4/912:25 p.m.
YWG
-
SXM
2 stops48h 55m
WestJet
Sun 13/93:20 p.m.
SXM
-
YWG
1 stop26h 55m
WestJet
Deal found 27/7C$ 625
Sat 12/98:00 a.m.
YWG
-
SXM
2 stops29h 20m
Multiple Airlines
Sat 26/96:00 p.m.
SXM
-
YWG
2 stops40h 59m
Multiple Airlines
Deal found 25/7C$ 687
Thu 3/94:10 p.m.
YWG
-
SXM
2 stops47h 50m
Air Canada
Sat 12/96:00 p.m.
SXM
-
YWG
1 stop21h 22m
Air Canada
Deal found 27/7C$ 807
Sun 6/96:05 p.m.
YWG
-
SXM
2 stops22h 00m
Multiple Airlines
Sun 13/93:20 p.m.
SXM
-
YWG
1 stop19h 25m
Multiple Airlines
Deal found 27/7C$ 913

Find 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 28 July 2026.

Round-trip from

C$ 557

One-way from

C$ 268
Air Canada
  • Air Canada
  • 12/9-26/9
  • 2 total stops
  • 29h 12m total
  • Winnipeg to Simpson Bay
Search Deals
Air Canada
  • Air Canada
  • 10/9
  • 2 total stops
  • 47h 50m total
  • Winnipeg to Simpson Bay
Search Deals

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 28 July 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
Quickest round-trip

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 12/9

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

1 stop11h 00m

Simpson Bay Princess Juliana

Sat 26/9

6:00 p.m.-9:59 a.m.

2 stops16h 59m

C$ 563

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 12/9

9:20 a.m.-4:05 p.m.

3 stops29h 45m

Simpson Bay Princess Juliana

Sat 26/9

6:10 p.m.-5:58 p.m.

3 stops24h 48m

C$ 1,577

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 8/9

5:44 p.m.-1:53 p.m.

2 stops19h 09m

Simpson Bay Princess Juliana

Wed 16/9

3:18 p.m.-11:51 a.m.

2 stops21h 33m

C$ 1,686

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 3/9

5:42 p.m.-1:53 p.m.

2 stops19h 11m

Simpson Bay Princess Juliana

Wed 16/9

3:18 p.m.-11:51 a.m.

2 stops21h 33m

C$ 1,721

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 6/9

3:58 p.m.-1:53 p.m.

2 stops20h 55m

Simpson Bay Princess Juliana

Fri 11/9

3:18 p.m.-11:51 a.m.

2 stops21h 33m

C$ 1,806

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 8/9

5:44 p.m.-1:53 p.m.

2 stops19h 09m

Simpson Bay Princess Juliana

Thu 10/9

3:18 p.m.-3:08 p.m.

2 stops24h 50m

C$ 1,806

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Wed 9/9

5:44 p.m.-1:53 p.m.

2 stops19h 09m

Simpson Bay Princess Juliana

Mon 14/9

3:18 p.m.-11:51 a.m.

2 stops21h 33m

C$ 1,841

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 5/9

6:40 a.m.-1:53 p.m.

2 stops30h 13m

Simpson Bay Princess Juliana

Thu 10/9

3:18 p.m.-4:54 p.m.

2 stops26h 36m

C$ 1,841

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 28/9

5:44 p.m.-1:53 p.m.

2 stops43h 09m

Simpson Bay Princess Juliana

Thu 1/10

3:18 p.m.-3:08 p.m.

2 stops24h 50m

C$ 1,843
Cheapest one-way

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 10/9

4:10 p.m.-5:00 p.m.

2 stops47h 50m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/7

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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 28 July 2026.
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
3,415 reviews
Check prices

Food

6.2

Entertainment

6.1

Boarding

7.4

Crew

7.9

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,415 reviews
WestJet
7.2
Good
3,415 reviews
Check prices

Food

6.2

Entertainment

6.1

Boarding

7.4

Crew

7.9

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 Air Canada and Delta fly from Winnipeg to Simpson Bay in about 11h. The time it takes to get you to your destination can typically vary by up to 8h 11m. 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$ 607), 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

Travelling to a place near Simpson Bay?

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

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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 28 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 607AverageC$ 890FlexibilityNo 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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