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Cheap flights from Winnipeg to Simpson Bay from C$ 314

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 13/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
29 may. — 5 jun.1
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 29 abril 2026.

dom. 21/64:25 p.m.
YWG
-
SXM
1 stop20h 55m
WestJet
jue. 25/63:20 p.m.
SXM
-
YWG
1 stop19h 25m
WestJet
Deal found 26/4C$ 538
vie. 28/810:30 p.m.
YWG
-
SXM
2 stops38h 50m
WestJet
dom. 6/93:20 p.m.
SXM
-
YWG
2 stops25h 05m
WestJet
Deal found 27/4C$ 590
vie. 28/85:10 p.m.
YWG
-
SXM
1 stop22h 50m
Multiple Airlines
dom. 6/93:20 p.m.
SXM
-
YWG
1 stop26h 55m
Multiple Airlines
Deal found 27/4C$ 859
mar. 26/52:00 p.m.
YWG
-
SXM
2 stops21h 33m
United Airlines
mar. 2/63:50 p.m.
SXM
-
YWG
2 stops31h 43m
United Airlines
Deal found 27/4C$ 911
jue. 24/91:25 p.m.
YWG
-
SXM
2 stops50h 35m
Multiple Airlines
lun. 5/101:00 p.m.
SXM
-
YWG
3 stops27h 19m
Multiple Airlines
Deal found 27/4C$ 1,288
mar. 26/58:45 p.m.
YWG
-
SXM
3 stops39h 45m
Multiple Airlines
mar. 2/611:40 a.m.
SXM
-
YWG
2 stops33h 09m
Multiple Airlines
Deal found 27/4C$ 1,426
jue. 24/95:38 p.m.
YWG
-
SXM
2 stops19h 12m
Delta
lun. 5/103:20 p.m.
SXM
-
YWG
2 stops21h 30m
Delta
Deal found 27/4C$ 1,498

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 29 abril 2026.

Round-trip from

C$ 538

One-way from

C$ 314
WestJet
  • WestJet
  • 21/6-25/6
  • 2 total stops
  • 40h 20m total
  • Winnipeg to Simpson Bay
Search Deals
13/6
  • 13/6
  • 1 total stop
  • 20h 10m 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 29 abril 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

dom. 21/6

10:45 a.m.-2:20 p.m.

1 stop26h 35m

Simpson Bay Princess Juliana

jue. 25/6

3:20 p.m.-9:45 a.m.

1 stop19h 25m

C$ 538

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

vie. 28/8

10:30 p.m.-2:20 p.m.

2 stops38h 50m

Simpson Bay Princess Juliana

dom. 6/9

3:20 p.m.-3:25 p.m.

2 stops25h 05m

C$ 590

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

vie. 28/8

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

1 stop22h 50m

Simpson Bay Princess Juliana

dom. 6/9

3:20 p.m.-5:15 p.m.

1 stop26h 55m

C$ 859

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

mar. 26/5

2:00 p.m.-12:33 p.m.

2 stops21h 33m

Simpson Bay Princess Juliana

mar. 2/6

3:50 p.m.-10:33 p.m.

2 stops31h 43m

C$ 911

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

jue. 24/9

1:25 p.m.-5:00 p.m.

2 stops50h 35m

Simpson Bay Princess Juliana

lun. 5/10

1:00 p.m.-3:19 p.m.

3 stops27h 19m

C$ 1,288
Cheapest one-way

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

sáb. 13/6

5:10 p.m.-2:20 p.m.

1 stop20h 10m

C$ 314
Quickest one-way

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

jue. 11/6

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

1 stop10h 50m

C$ 340

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

sáb. 13/6

8:45 a.m.-12:33 p.m.

2 stops50h 48m

C$ 373

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

sáb. 13/6

7:10 p.m.-2:20 p.m.

3 stops42h 10m

C$ 376

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

jue. 11/6

11:40 a.m.-10:50 a.m.

3 stops22h 10m

C$ 519

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

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 29 abril 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
3,328 reviews
Check prices

Crew

7.9

Food

6.2

Comfort

7.0

Entertainment

6.1

Boarding

7.4

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
3,328 reviews
WestJet
7.2
Good
3,328 reviews
Check prices

Crew

7.9

Food

6.2

Comfort

7.0

Entertainment

6.1

Boarding

7.4

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 WestJet fly from Winnipeg to Simpson Bay in about 26h 35m. 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$ 588), 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 29 abril 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 588AverageC$ 861FlexibilityNo 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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