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Cheap Flights from Winnipeg to St Maarten

Compare Winnipeg to St Maarten flight deals

Find the cheapest month or even day of the year to fly to St Maarten

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Flight deals from Winnipeg to St Maarten

Looking for a cheap last-minute deal or the best return flight from Winnipeg Airport to St Maarten Airport? If you want to travel next month, return fares start from $1,953. Find the lowest prices on one-way and return tickets right here.
Philipsburg.$768 per passenger.Departing Fri, 4 Sep, returning Sat, 19 Sep.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Fri, 4 Sep, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 19 Sep, arriving in Winnipeg.Price includes taxes and charges.From $768, select.
Philipsburg.$857 per passenger.Departing Tue, 19 Jan, returning Wed, 27 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Tue, 19 Jan, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Wed, 27 Jan, arriving in Winnipeg.Price includes taxes and charges.From $857, select.
Philipsburg.$1,120 per passenger.Departing Wed, 10 Feb, returning Wed, 17 Feb.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 10 Feb, arriving in St Maarten.Inbound indirect flight with WestJet, departs from St Maarten on Wed, 17 Feb, arriving in Winnipeg.Price includes taxes and charges.From $1,120, select.
Philipsburg.$1,953 per passenger.Departing Mon, 24 Aug, returning Mon, 31 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Mon, 24 Aug, arriving in St Maarten.Inbound indirect flight with WestJet, departs from St Maarten on Mon, 31 Aug, arriving in Winnipeg.Price includes taxes and charges.From $1,953, select.
Philipsburg.$2,092 per passenger.Departing Mon, 28 Dec, returning Tue, 5 Jan.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Winnipeg on Mon, 28 Dec, arriving in St Maarten.Inbound indirect flight with WestJet, departs from St Maarten on Tue, 5 Jan, arriving in Winnipeg.Price includes taxes and charges.From $2,092, select.

Find the cheapest month to fly from Winnipeg to St Maarten

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Winnipeg to St Maarten flights are currently cheapest in September.
Jul
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Aug
from $1,953
Sep
from $768
Oct
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Nov
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Dec
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Jan
from $857
Feb
from $1,120
Mar
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Apr
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May
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Jun
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Winnipeg to St Maarten: Alternative routes

Compare routes from Winnipeg to Philipsburg below. You may find an airport to fly into that's cheaper, faster, or easier than St Maarten.

St Maarten

7km from central Philipsburg
ClosestCheapest
from $768
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Winnipeg to Philipsburg: Flight information

The things to know before you go.
Cheapest flight found$768
Cheapest month to flySeptember

Finding cheap flights from Winnipeg to St Maarten: Frequently asked questions

The best price we found for a return flight from Winnipeg to St Maarten is $768. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Winnipeg to St Maarten. But we found flights with one or more stops from $768.
As of July 2026, there are no flights flying from Winnipeg to St Maarten.
The cheapest month to fly from Winnipeg to St Maarten is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to St Maarten Airport on Friday, 4 September 2026.
No airlines currently offer direct flights between Winnipeg Airport and St Maarten Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to St Maarten but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Philipsburg is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Air Canada offers the cheapest flight tickets to St Maarten.

Flying from Winnipeg James Armstrong Richardson International Airport (YWG) to Princess Juliana International Airport (SXM): what you need to know

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This way, you can comfortably catch your YWG to SXM flight.

  • If you're taking off during a bank holiday or other peak periods, give yourself more time. A good rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

How to find the cheapest flights from Winnipeg James Armstrong Richardson International Airport (YWG) to Princess Juliana International Airport (SXM)

  • Right now, $343 is the lowest price we've found for a one-way Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport flight. The best price for a return ticket is $768. Keep in mind that fares may change due to availability at the time of booking.

  • It's a good idea to book ahead of time if you want to find cheap tickets from YWG to SXM. That's because flight prices are based on demand, which tends to rise closer to the date of departure.

  • Getting cheap flights from Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport is easier if you can be flexible with your trip dates. Use the 'Whole month' search function to see the best prices across every month and snap up a great deal.

  • Finding cheap flights from YWG to SXM is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know as soon as there's a better deal.

  • Discover the right flight for you by using the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about Winnipeg James Armstrong Richardson International Airport (YWG)

  • YWG is located at 2000 Wellington Avenue.

  • 61.28% of flights that depart Winnipeg James Armstrong Richardson International Airport make it to their destination on time.

  • To reach Winnipeg James Armstrong Richardson International Airport from central Winnipeg, it'll take around 15 minutes if you're going by car. Of course, this depends on traffic conditions. It's approximately 8 kilometres from the airport to the city centre.

  • Planning to take public transport? Expect a trip time of around 55 minutes.

  • Get your travels off to a stress-free start by staying near YWG. Whether you're catching an early flight from Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport or just don't like being rushed, these hotels have you covered:

Arriving at Princess Juliana International Airport (SXM)

Getting from Princess Juliana International Airport (SXM) to central Philipsburg

  • From Princess Juliana International Airport, Philipsburg is approximately 11 kilometres away. It takes around 25 minutes to reach the centre driving.

When to fly to Princess Juliana International Airport (SXM)

  • The quietest month for a flight from Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport is April, while February is the busiest. Pick the best time to visit Philipsburg based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • Lock in your flight from Winnipeg James Armstrong Richardson International Airport to Princess Juliana International Airport for September if you'd like to visit Philipsburg during its warmest month. Expect temperatures of between 25ºC and 29ºC.

  • February sees average temperatures of between 21ºC and 26ºC. Search for cheap tickets from YWG to SXM sometime around then if you like travelling in cooler conditions.

Plan the rest of your trip from Winnipeg to Philipsburg

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.