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Cheap flights from Winnipeg to St. Maarten from C$ 1,462

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap 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 30 October 2025.

Round-trip from

C$ 649
WestJet
  • WestJet
  • 24/1-6/2
  • 3 total stops
  • 26h 40m total
  • Winnipeg to St. Maarten
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Find 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 30 October 2025.

Mon 3/118:20 p.m.YWG - SXM
1 stop17h 01mMultiple Airlines
Wed 5/1110:45 a.m.SXM - YWG
2 stops15h 57mMultiple Airlines
Deal found 29/10C$ 1,789
Sun 28/128:05 p.m.YWG - SXM
1 stop17h 16mWestJet
Fri 2/14:20 p.m.SXM - YWG
1 stop10h 15mWestJet
Deal found 29/10C$ 2,043
Mon 3/115:30 a.m.YWG - SXM
2 stops30h 20mAir Canada
Wed 5/112:52 p.m.SXM - YWG
2 stops32h 52mAir Canada
Deal found 29/10C$ 2,054
Sun 28/122:20 p.m.YWG - SXM
2 stops45h 30mUnited Airlines
Fri 2/14:55 p.m.SXM - YWG
2 stops29h 56mUnited Airlines
Deal found 30/10C$ 2,343
Sun 28/127:05 a.m.YWG - SXM
1 stop30h 55mAir Canada
Fri 2/12:52 p.m.SXM - YWG
2 stops51h 43mAir Canada
Deal found 29/10C$ 2,906
Sun 28/1212:10 p.m.YWG - SXM
3 stops26h 23mAmerican Airlines
Fri 2/13:28 p.m.SXM - YWG
3 stops34h 07mAmerican Airlines
Deal found 29/10C$ 4,154

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 30 October 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

Sun 12/4

8:30 a.m.-12:29 p.m.

2 stops26h 59m

Simpson Bay Princess Juliana

Wed 15/4

1:35 p.m.-8:48 p.m.

2 stops32h 13m

C$ 1,462

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 12/4

7:15 a.m.-2:50 p.m.

1 stop30h 35m

Simpson Bay Princess Juliana

Wed 15/4

1:35 p.m.-9:42 a.m.

2 stops21h 07m

C$ 1,563

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

8:05 p.m.-3:21 p.m.

1 stop17h 16m

Simpson Bay Princess Juliana

Fri 2/1

4:20 p.m.-12:35 a.m.

1 stop10h 15m

C$ 2,043

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

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

2 stops45h 30m

Simpson Bay Princess Juliana

Fri 2/1

4:55 p.m.-8:51 p.m.

2 stops29h 56m

C$ 2,343

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:05 a.m.-4:00 p.m.

1 stop30h 55m

Simpson Bay Princess Juliana

Fri 2/1

2:52 p.m.-4:35 p.m.

2 stops51h 43m

C$ 2,906

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

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 30 October 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
3,152 reviews
Check prices

Comfort

7.1

Entertainment

6.1

Food

6.2

Overall

7.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon
WestJet
7.2
Good
3,152 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Comfort

7.1

Entertainment

6.1

Food

6.2

Overall

7.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

YYJ - YVR

everything was good except we were so delayed we had to sleep on the floor in the vancouver airport … we were stranded there for 12 hours, no vouchers, no compensation, just a cold floor and we arrived at our final destination the following afternoon

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 59m. The distance from Winnipeg to St. Maarten is about 4661 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 570AverageC$ 823FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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

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

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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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