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Cheap flights from Winnipeg to St. Maarten from C$ 223

YWG — SXM
12 Oct — 19 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to St. Maarten

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to St. Maarten

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 St. Maarten

Round-trip from

C$ 449

One-way from

C$ 223
WestJet
  • WestJet
  • 27/11-1/12
  • 3 total stops
  • 63h 09m total
  • Winnipeg to St. Maarten
Search Deals
Air Canada
  • Air Canada
  • 26/10-31/12
  • 1 total stop
  • 8h 30m total
  • Winnipeg to St. Maarten
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to St. Maarten 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 St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Winnipeg with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to St. Maarten

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing St. Maarten

Read through reviews of airlines operating flights from Winnipeg to St. Maarten, such as WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,445 reviews
Check prices

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Food

6.2

Comfort

7.1

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

Crew

7.9

Overall

7.2

Entertainment

6.1

Boarding

7.4

Food

6.2

Comfort

7.1

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

  • What airport do you fly from for flights from Winnipeg to St. Maarten?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly out of when you book flights from Winnipeg to St. Maarten.

  • How long is the flight from Winnipeg to St. Maarten?

    Departing from Winnipeg to St. Maarten will take you 29h 30m. The distance from Winnipeg to St. Maarten is about 4661 km.

  • Can I find deals for flights from Winnipeg to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Winnipeg to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to St. Maarten.

  • Can I find deals for business class flights from Winnipeg to St. Maarten?

    Yes. Cheapflights offers flight deals from Winnipeg to St. Maarten 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

Top airline flying from Winnipeg to St. Maarten

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

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