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Cheap flights from Winnipeg to Simpson Bay from C$ 311

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 20/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
9 Apr — 16 Apr1
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 10 March 2026.

Sun 12/45:00 a.m.
YWG
-
SXM
1 stop8h 17m
WestJet
Thu 16/43:20 p.m.
SXM
-
YWG
2 stops27h 45m
WestJet
Deal found 6/3C$ 766
Wed 22/412:55 p.m.
YWG
-
SXM
2 stops48h 22m
WestJet
Wed 29/43:50 p.m.
SXM
-
YWG
2 stops21h 02m
WestJet
Deal found 8/3C$ 851
Fri 3/49:00 p.m.
YWG
-
SXM
2 stops40h 17m
Multiple Airlines
Mon 6/42:35 p.m.
SXM
-
YWG
3 stops44h 32m
Multiple Airlines
Deal found 10/3C$ 998
Fri 3/49:00 p.m.
YWG
-
SXM
2 stops40h 17m
WestJet
Mon 6/43:20 p.m.
SXM
-
YWG
1 stop21h 12m
WestJet
Deal found 10/3C$ 1,064
Wed 22/49:00 p.m.
YWG
-
SXM
2 stops40h 17m
Multiple Airlines
Wed 29/410:30 a.m.
SXM
-
YWG
3 stops34h 45m
Multiple Airlines
Deal found 8/3C$ 1,241
Mon 19/106:05 p.m.
YWG
-
SXM
3 stops43h 45m
Multiple Airlines
Sat 24/105:00 p.m.
SXM
-
YWG
2 stops32h 45m
Multiple Airlines
Deal found 6/3C$ 1,636
Tue 10/35:00 a.m.
YWG
-
SXM
1 stop8h 17m
WestJet
Mon 16/33:20 p.m.
SXM
-
YWG
1 stop28h 49m
WestJet
Deal found 6/3C$ 1,682

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 10 March 2026.

Round-trip from

C$ 766

One-way from

C$ 311
WestJet
  • WestJet
  • 12/4-16/4
  • 3 total stops
  • 36h 02m total
  • Winnipeg to Simpson Bay
Search Deals
Air Canada
  • Air Canada
  • 20/4
  • 1 total stop
  • 8h 25m 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 10 March 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 - SXM

YWGSXM

Winnipeg

Sun 12/4

9:15 p.m.-2:17 p.m.

2 stops40h 02m

Simpson Bay Princess Juliana

Thu 16/4

3:20 p.m.-12:40 a.m.

2 stops34h 20m

C$ 766

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Wed 22/4

12:55 p.m.-2:17 p.m.

2 stops48h 22m

Simpson Bay Princess Juliana

Wed 29/4

3:50 p.m.-11:52 a.m.

2 stops21h 02m

C$ 851

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 3/4

9:00 p.m.-2:17 p.m.

2 stops40h 17m

Simpson Bay Princess Juliana

Mon 6/4

2:35 p.m.-10:07 a.m.

3 stops44h 32m

C$ 998
Quickest round-trip

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 3/4

9:00 p.m.-2:17 p.m.

2 stops40h 17m

Simpson Bay Princess Juliana

Mon 6/4

3:20 p.m.-11:32 a.m.

1 stop21h 12m

C$ 1,064
Cheapest one-way
Quickest one-way

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 20/4

5:30 a.m.-2:55 p.m.

1 stop8h 25m

C$ 311

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 20/4

5:10 p.m.-11:26 a.m.

2 stops41h 16m

C$ 339

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/3

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.
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 10 March 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
3,288 reviews
Check prices

Overall

7.2

Entertainment

6.1

Boarding

7.4

Food

6.2

Comfort

7.0

Crew

7.9

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
3,288 reviews
WestJet
7.2
Good
3,288 reviews
Check prices

Overall

7.2

Entertainment

6.1

Boarding

7.4

Food

6.2

Comfort

7.0

Crew

7.9

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 WestJet fly from Winnipeg to Simpson Bay in about 40h 02m. The time it takes to get you to your destination can typically vary by up to . There are 4661 km between Winnipeg and Simpson Bay.

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

    According to our current data, WestJet (C$ 584), 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

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.
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 10 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 584AverageC$ 856FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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