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Cheap flights from Winnipeg to St. Maarten from C$ 244

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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
23 Jan — 30 Jan1
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
Explore the most affordable flight options available from Winnipeg to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 December 2025.

Sun 28/1212:20 p.m.YWG - SXM
1 stop25h 01mWestJet
Fri 2/14:20 p.m.SXM - YWG
1 stop10h 15mWestJet
Deal found 23/12C$ 2,241
Sun 28/126:00 a.m.YWG - SXM
2 stops29h 26mAmerican Airlines
Fri 2/13:28 p.m.SXM - YWG
3 stops34h 07mAmerican Airlines
Deal found 23/12C$ 5,783

Find flight deals from Winnipeg to St. Maarten

Keep the following information in mind while searching for Winnipeg to St. Maarten flight deals. Data was last updated 24 December 2025.

Round-trip from

C$ 599

One-way from

C$ 244
WestJet
  • WestJet
  • 19/1-22/1
  • 2 total stops
  • 46h 08m total
  • Winnipeg to St. Maarten
Search Deals
5/2
  • 5/2
  • 3 total stops
  • 39h 15m total
  • Winnipeg to St. Maarten
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to St. Maarten 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 24 December 2025.
Use the filters below to find and compare flights from Winnipeg to St. Maarten that are best for you.

Fly from

Winnipeg

Fly to

St. Maarten

Route

Depart

Return

Price

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 19/1

10:55 a.m.-3:21 p.m.

2 stops26h 26m

Simpson Bay Princess Juliana

Thu 22/1

4:20 p.m.-11:53 a.m.

2 stops21h 33m

C$ 599

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 23/1

12:55 p.m.-3:21 p.m.

2 stops48h 26m

Simpson Bay Princess Juliana

Tue 27/1

4:20 p.m.-11:50 p.m.

2 stops33h 30m

C$ 661

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 17/1

2:20 p.m.-1:50 p.m.

2 stops21h 30m

Simpson Bay Princess Juliana

Sat 24/1

5:00 p.m.-11:57 a.m.

2 stops20h 57m

C$ 743

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 17/1

12:55 p.m.-3:21 p.m.

2 stops24h 26m

Simpson Bay Princess Juliana

Sat 24/1

3:15 p.m.-3:07 p.m.

3 stops25h 52m

C$ 774

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 5/2

9:00 p.m.-2:15 p.m.

3 stops39h 15m

C$ 244

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 7/2

9:00 p.m.-2:15 p.m.

3 stops39h 15m

C$ 259

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 7/2

8:15 a.m.-2:40 p.m.

1 stop28h 25m

C$ 329

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 5/2

8:05 p.m.-3:17 p.m.

1 stop17h 12m

C$ 409

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/12

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
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.

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

Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated 24 December 2025.
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
3,216 reviews
Check prices

Overall

7.2

Entertainment

6.1

Crew

7.9

Food

6.2

Comfort

7.0

Boarding

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Nov 2025

YQU - YYC

After first flight cancelled they barely accommodated our flight to get to our destination, after 36 hours of travel and long layovers we arrived but the worst experience ever! I will definitely put claims in of the lost upgrades and lost time and money we had!!!
WestJet
7.2
Good
3,216 reviews
WestJet
7.2
Good
3,216 reviews
Check prices

Overall

7.2

Entertainment

6.1

Crew

7.9

Food

6.2

Comfort

7.0

Boarding

7.4

Reviews

1 / 20
2.0
Mediocre

Anonymous,Nov 2025

YQU - YYC

After first flight cancelled they barely accommodated our flight to get to our destination, after 36 hours of travel and long layovers we arrived but the worst experience ever! I will definitely put claims in of the lost upgrades and lost time and money we had!!!

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 26h 26m. 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

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Top airline flying from Winnipeg to St. Maarten

Discover the top airline that operate flights from Winnipeg to St. Maarten. 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 24 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 560AverageC$ 820FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to St. Maarten?

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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to St. Maarten?

Cheapflights helps you find that perfect flight to St. Maarten from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Winnipeg to St. Maarten with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to St. Maarten flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Winnipeg to St. Maarten become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to St. Maarten flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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