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Cheap flights from Winnipeg to Simpson Bay from C$ 770

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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SXM
2 Apr — 9 Apr1
1 adult

Cheap flight deals from Winnipeg to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 28 March 2025.

Round-trip from

C$ 770
WestJet
  • WestJet
  • 11/4-15/4
  • 3 total stops
  • 84h 40m total
  • Winnipeg to Simpson Bay
Search Deals

Find flight deals from Winnipeg to Simpson Bay

Cheapest flights from Winnipeg to Simpson Bay
Explore the most affordable flight options available from Winnipeg to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 March 2025.

Fri 11/48:15 a.m.YWG - SXM
2 stops53h 01mWestJet
Tue 15/43:10 p.m.SXM - YWG
1 stop31h 39mWestJet
Deal found 28/3C$ 770
Fri 11/45:00 a.m.YWG - SXM
1 stop29h 15mMultiple Airlines
Tue 15/43:10 p.m.SXM - YWG
1 stop31h 39mMultiple Airlines
Deal found 28/3C$ 989
Wed 24/124:30 p.m.YWG - SXM
2 stops19h 21mUnited Airlines
Wed 31/124:55 p.m.SXM - YWG
2 stops22h 08mUnited Airlines
Deal found 28/3C$ 1,761
Sun 28/123:30 p.m.YWG - SXM
2 stops22h 45mAir Canada
Fri 2/15:15 p.m.SXM - YWG
2 stops23h 58mAir Canada
Deal found 28/3C$ 2,310

Cheapflights Fare Finder

Customize your flight search to find flights from Winnipeg to Simpson Bay 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 28 March 2025.
Use the filters below to find and compare flights from Winnipeg to Simpson Bay that are best for you.

Fly from

Winnipeg

Fly to

Simpson Bay

Route

Depart

Return

Price

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 11/4

8:15 a.m.-2:16 p.m.

2 stops53h 01m

Simpson Bay Princess Juliana

Tue 15/4

3:10 p.m.-9:49 p.m.

1 stop31h 39m

C$ 770

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Fri 11/4

5:00 a.m.-11:15 a.m.

1 stop29h 15m

Simpson Bay Princess Juliana

Tue 15/4

3:10 p.m.-9:49 p.m.

1 stop31h 39m

C$ 989

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/3

Best time to book a flight from Winnipeg to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 Simpson Bay

What is the cheapest time of day to fly from YWG to SXM?

Find hourly flight availability from Winnipeg to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 March 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Simpson Bay at noon. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated 28 March 2025.
WestJet
7.2
Good
2,785 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Crew

7.9

Food

6.2

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.
WestJet
7.2
Good
2,785 reviews
WestJet
7.2
Good
2,785 reviews
Check prices

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Crew

7.9

Food

6.2

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.

Related info for your journey

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

  • What is the cheapest airline to fly from Winnipeg to Simpson Bay round-trip?

    According to our current data, WestJet (C$ 770), offers the cheapest pricing from Winnipeg to Simpson Bay.

  • Can I find deals for flights from Winnipeg to Simpson Bay that include hotel bookings?

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

  • How can I find direct flights from Winnipeg to Simpson Bay?

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

  • Can I find deals for business class flights from Winnipeg to Simpson Bay?

    Yes. Cheapflights offers flight deals from Winnipeg to Simpson Bay 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 Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Simpson Bay (average of C$ 324). Flying from Winnipeg to Simpson Bay in July is currently the most expensive (average of C$ 670). 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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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top airline flying from Winnipeg to Simpson Bay

Discover the top airline that operate flights from Winnipeg to Simpson Bay. 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 28 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 583AverageC$ 799FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Simpson Bay?

Cheapflights makes it easy to find Winnipeg to Simpson Bay flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Simpson Bay?

Cheapflights simply makes it quick and affordable to book flights from Winnipeg to Simpson Bay by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Winnipeg to Simpson Bay with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Simpson Bay, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Simpson Bay become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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