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Cheap flights from Winnipeg to Simpson Bay from C$ 223

YWG — SXM
12 Oct — 19 Oct1
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

Fri 27/115:00 a.m. -
1 stop29h 30m
Tue 1/124:20 p.m. -
2 stops33h 39m
Deal found 10/9C$ 449
Wed 21/107:00 a.m. -
2 stops30h 10m
Thu 29/103:20 p.m. -
1 stop10h 24m
Deal found 11/9C$ 535
Wed 21/107:45 a.m. -
1 stop29h 25m
Thu 29/103:20 p.m. -
1 stop18h 55m
Deal found 11/9C$ 614
Thu 24/126:00 a.m. -
2 stops31h 25m
Tue 29/124:20 p.m. -
2 stops33h 39m
Deal found 11/9C$ 630

Find flight deals from Winnipeg to Simpson Bay

Round-trip from

C$ 449

One-way from

C$ 223
WestJet
  • WestJet
  • 27/11-1/12
  • 3 total stops
  • 63h 09m total
  • Winnipeg to Simpson Bay
Search Deals
Air Canada
  • Air Canada
  • 26/10-31/12
  • 1 total stop
  • 8h 30m 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
Quickest round-trip

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

5:15 a.m.-2:45 p.m.

1 stop8h 30m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 223

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Sun 25/10

1:30 p.m.-2:45 p.m.

2 stops24h 15m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 230

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Sun 25/10

10:00 a.m.-2:25 p.m.

1 stop27h 25m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 231

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Sun 25/10

3:45 p.m.-2:25 p.m.

3 stops21h 40m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 357

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Fri 27/11

5:00 a.m.-12:30 p.m.

1 stop29h 30m

Simpson Bay Princess Juliana

Tue 1/12

4:20 p.m.-11:05 a.m.

1 stop20h 45m

C$ 461

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Mon 26/10

11:05 a.m.-2:25 p.m.

2 stops26h 20m

Simpson Bay Princess Juliana

Wed 31/12

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

Nonstop0h 00m

C$ 511

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Wed 21/10

7:00 a.m.-2:10 p.m.

2 stops30h 10m

Simpson Bay Princess Juliana

Thu 29/10

3:20 p.m.-1:00 a.m.

2 stops34h 40m

C$ 546

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Wed 21/10

7:45 a.m.-2:10 p.m.

1 stop29h 25m

Simpson Bay Princess Juliana

Thu 29/10

3:20 p.m.-9:15 a.m.

1 stop18h 55m

C$ 614

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Thu 24/12

12:10 p.m.-3:25 p.m.

2 stops25h 15m

Simpson Bay Princess Juliana

Tue 29/12

4:20 p.m.-7:50 p.m.

1 stop29h 30m

C$ 636

WinnipegSimpson Bay

YWG Winnipeg - SXM Simpson Bay Princess Juliana

YWGSXM

Winnipeg

Thu 24/12

6:55 p.m.-3:45 p.m.

1 stop18h 50m

Simpson Bay Princess Juliana

Mon 28/12

4:45 p.m.-6:25 p.m.

2 stops51h 40m

C$ 750

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 12 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

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

Overall

7.2

Crew

7.9

Food

6.2

Entertainment

6.1

Comfort

7.1

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,445 reviews
WestJet
7.2
Good
3,445 reviews
Check prices

Overall

7.2

Crew

7.9

Food

6.2

Entertainment

6.1

Comfort

7.1

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

Related info for your journey

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

    Airlines like WestJet fly from Winnipeg to Simpson Bay in about 29h 30m. 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$ 596), 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

Simpson Bay Princess Juliana Airport car rentals

Top airline flying from Winnipeg to Simpson Bay

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 596AverageC$ 854FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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?

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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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