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Cheap flights from Winnipeg to St. Maarten from C$ 296

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 28/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
15 Oct — 22 Oct1
1 adult
1 adult, Economy

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 15 September 2025.

Round-trip from

C$ 660

One-way from

C$ 296
WestJet
  • WestJet
  • 21/11-5/12
  • 4 total stops
  • 70h 07m total
  • Winnipeg to St. Maarten
Search Deals
Air Canada
  • Air Canada
  • 28/10
  • 2 total stops
  • 51h 35m total
  • Winnipeg to St. Maarten
Search Deals

Find flight deals from Winnipeg to St. Maarten

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 15 September 2025.

Fri 21/119:00 p.m.YWG - SXM
2 stops40h 21mWestJet
Fri 5/124:20 p.m.SXM - YWG
2 stops29h 46mWestJet
Deal found 13/9C$ 660
Fri 21/116:15 a.m.YWG - SXM
2 stops55h 06mMultiple Airlines
Fri 5/125:00 p.m.SXM - YWG
1 stop21h 39mMultiple Airlines
Deal found 13/9C$ 691
Sat 11/103:15 p.m.YWG - SXM
2 stops20h 59mWestJet
Sun 26/103:20 p.m.SXM - YWG
2 stops25h 01mWestJet
Deal found 15/9C$ 1,029
Sat 11/105:15 p.m.YWG - SXM
3 stops25h 15mMultiple Airlines
Sun 26/103:20 p.m.SXM - YWG
2 stops19h 48mMultiple Airlines
Deal found 15/9C$ 1,109
Sun 28/128:05 p.m.YWG - SXM
1 stop17h 16mWestJet
Fri 2/14:20 p.m.SXM - YWG
1 stop21h 15mWestJet
Deal found 13/9C$ 1,728
Sun 28/128:40 a.m.YWG - SXM
2 stops51h 10mUnited Airlines
Fri 2/14:55 p.m.SXM - YWG
2 stops32h 49mUnited Airlines
Deal found 15/9C$ 1,753
Sun 28/127:30 a.m.YWG - SXM
1 stop29h 20mDelta
Fri 2/11:50 p.m.SXM - YWG
2 stops24h 04mDelta
Deal found 15/9C$ 2,097
Sun 28/121:45 p.m.YWG - SXM
2 stops24h 15mAir Canada
Fri 2/12:52 p.m.SXM - YWG
2 stops23h 47mAir Canada
Deal found 14/9C$ 2,484

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 15 September 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

Fri 21/11

9:00 p.m.-3:21 p.m.

2 stops40h 21m

Simpson Bay Princess Juliana

Fri 5/12

4:20 p.m.-8:06 p.m.

2 stops29h 46m

C$ 660

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 21/11

6:15 a.m.-3:21 p.m.

2 stops55h 06m

Simpson Bay Princess Juliana

Fri 5/12

5:00 p.m.-12:39 p.m.

1 stop21h 39m

C$ 691

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 11/10

3:15 p.m.-1:14 p.m.

2 stops20h 59m

Simpson Bay Princess Juliana

Sun 26/10

3:20 p.m.-3:21 p.m.

2 stops25h 01m

C$ 1,029

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 11/10

5:15 p.m.-7:30 p.m.

3 stops25h 15m

Simpson Bay Princess Juliana

Sun 26/10

3:20 p.m.-10:08 a.m.

2 stops19h 48m

C$ 1,109

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.-11:35 a.m.

1 stop21h 15m

C$ 1,728

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

8:40 a.m.-1:50 p.m.

2 stops51h 10m

Simpson Bay Princess Juliana

Fri 2/1

4:55 p.m.-11:44 p.m.

2 stops32h 49m

C$ 1,753

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:30 a.m.-2:50 p.m.

1 stop29h 20m

Simpson Bay Princess Juliana

Fri 2/1

1:50 p.m.-11:54 a.m.

2 stops24h 04m

C$ 2,097

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 28/10

8:15 a.m.-12:50 p.m.

2 stops51h 35m

C$ 296

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 30/10

6:00 a.m.-3:00 p.m.

2 stops32h 00m

C$ 296

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Thu 30/10

8:05 p.m.-2:21 p.m.

1 stop17h 16m

C$ 315

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 13 results
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
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 15 September 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
3,091 reviews
Check prices

Crew

7.9

Food

6.2

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Overall

7.2

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
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Crew

7.9

Food

6.2

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Overall

7.2

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 40h 21m. 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.

  • What is the cheapest month to book a flight from Winnipeg to St. Maarten?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to St. Maarten (average of C$ 324). Flying from Winnipeg to St. Maarten in February is currently the most expensive (average of C$ 584). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 15 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 564AverageC$ 776FlexibilityNo 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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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to St. Maarten?

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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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