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Cheap flights from Winnipeg to Simpson Bay from C$ 614

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Simpson Bay departing on 31/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Winnipeg to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:05 p.m. - 1:50 p.m.
YWG
-
SXM
18h 45m
1 stop
WestJet Logo
2:40 p.m. - 9:45 a.m.
SXM
-
YWG
20h 05m
1 stop
C$ 614WestJet
Sun, 31 May - Thu, 4 Jun
WestJet Logo
9:05 p.m. - 1:50 p.m.
YWG
-
SXM
15h 45m
2 stops
WestJet Logo
2:40 p.m. - 3:25 p.m.
SXM
-
YWG
25h 45m
2 stops
C$ 758WestJet
Sun, 31 May - Thu, 4 Jun
United Airlines Logo
8:45 a.m. - 12:33 p.m.
YWG
-
SXM
26h 48m
2 stops
United Airlines Logo
3:50 p.m. - 11:52 a.m.
SXM
-
YWG
21h 02m
2 stops
C$ 808United Airlines
Sat, 25 Apr - Wed, 29 Apr
United Airlines Logo
8:45 a.m. - 12:33 p.m.
YWG
-
SXM
26h 48m
2 stops
United Airlines Logo
3:50 p.m. - 11:52 a.m.
SXM
-
YWG
45h 02m
2 stops
C$ 833United Airlines
Sat, 25 Apr - Wed, 29 Apr
Air Canada Logo
5:30 a.m. - 2:55 p.m.
YWG
-
SXM
8h 25m
1 stop
Air Canada Logo
1:35 p.m. - 8:17 p.m.
SXM
-
YWG
31h 42m
2 stops
C$ 1,780Air Canada
Sat, 25 Apr - Wed, 29 Apr
Air Canada Logo
5:30 a.m. - 2:55 p.m.
YWG
-
SXM
8h 25m
1 stop
Air Canada Logo
1:35 p.m. - 8:17 p.m.
SXM
-
YWG
31h 42m
2 stops
C$ 1,786Air Canada
Sat, 25 Apr - Wed, 29 Apr
Air Canada Logo
5:30 a.m. - 2:55 p.m.
YWG
-
SXM
8h 25m
1 stop
Air Canada Logo
1:35 p.m. - 8:17 p.m.
SXM
-
YWG
31h 42m
2 stops
C$ 1,790Air Canada
Sat, 25 Apr - Wed, 29 Apr
Air Canada Logo
6:00 a.m. - 2:55 p.m.
YWG
-
SXM
55h 55m
2 stops
Air Canada Logo
1:35 p.m. - 8:17 p.m.
SXM
-
YWG
31h 42m
2 stops
C$ 1,890Air Canada
Sat, 25 Apr - Wed, 29 Apr

United Airlines flights from Winnipeg to Simpson Bay

Our best United Airlines deals on Winnipeg to Simpson Bay flight tickets
United Airlines
25 Apr
YWG8:45 a.m.Winnipeg
26h 48m
2 stops
SXM12:33 p.m.Simpson Bay Princess Juliana
29 Apr
SXM3:50 p.m.Simpson Bay Princess Juliana
21h 02m
2 stops
YWG11:52 a.m.Winnipeg
C$ 808
United Airlines
25 Apr
YWG8:45 a.m.Winnipeg
26h 48m
2 stops
SXM12:33 p.m.Simpson Bay Princess Juliana
29 Apr
SXM3:50 p.m.Simpson Bay Princess Juliana
45h 02m
2 stops
YWG11:52 a.m.Winnipeg
C$ 833
United Airlines
2 Apr
YWG7:05 p.m.Winnipeg
18h 38m
2 stops
SXM2:43 p.m.Simpson Bay Princess Juliana
30 Apr
SXM1:35 p.m.Simpson Bay Princess Juliana
23h 17m
2 stops
YWG11:52 a.m.Winnipeg
C$ 1,685

Air Canada flights from Winnipeg to Simpson Bay

Our best Air Canada deals on Winnipeg to Simpson Bay flight tickets
Air Canada
25 Apr
YWG5:30 a.m.Winnipeg
8h 25m
1 stop
SXM2:55 p.m.Simpson Bay Princess Juliana
29 Apr
SXM1:35 p.m.Simpson Bay Princess Juliana
31h 42m
2 stops
YWG8:17 p.m.Winnipeg
C$ 1,780
Air Canada
25 Apr
YWG5:30 a.m.Winnipeg
8h 25m
1 stop
SXM2:55 p.m.Simpson Bay Princess Juliana
29 Apr
SXM1:35 p.m.Simpson Bay Princess Juliana
31h 42m
2 stops
YWG8:17 p.m.Winnipeg
C$ 1,786
Air Canada
25 Apr
YWG5:30 a.m.Winnipeg
8h 25m
1 stop
SXM2:55 p.m.Simpson Bay Princess Juliana
29 Apr
SXM1:35 p.m.Simpson Bay Princess Juliana
31h 42m
2 stops
YWG8:17 p.m.Winnipeg
C$ 1,790

momondo 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, momondo users made 96,600 searches. Data last updated 28 March 2026.
Use the filters below to find and compare flights from Winnipeg to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 31/5

6:05 p.m.-1:50 p.m.

1 stop18h 45m

Simpson Bay Princess Juliana

Thu 4/6

2:40 p.m.-9:45 a.m.

1 stop20h 05m

C$ 614

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 31/5

9:05 p.m.-1:50 p.m.

2 stops15h 45m

Simpson Bay Princess Juliana

Thu 4/6

2:40 p.m.-3:25 p.m.

2 stops25h 45m

C$ 758

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

8:45 a.m.-12:33 p.m.

2 stops26h 48m

Simpson Bay Princess Juliana

Wed 29/4

3:50 p.m.-11:52 a.m.

2 stops21h 02m

C$ 808

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

8:45 a.m.-12:33 p.m.

2 stops26h 48m

Simpson Bay Princess Juliana

Wed 29/4

3:50 p.m.-11:52 a.m.

2 stops45h 02m

C$ 833

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

5:30 a.m.-2:55 p.m.

1 stop8h 25m

Simpson Bay Princess Juliana

Wed 29/4

1:35 p.m.-8:17 p.m.

2 stops31h 42m

C$ 1,780

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

5:30 a.m.-2:55 p.m.

1 stop8h 25m

Simpson Bay Princess Juliana

Wed 29/4

1:35 p.m.-8:17 p.m.

2 stops31h 42m

C$ 1,786

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

5:30 a.m.-2:55 p.m.

1 stop8h 25m

Simpson Bay Princess Juliana

Wed 29/4

1:35 p.m.-8:17 p.m.

2 stops31h 42m

C$ 1,790

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 25/4

6:00 a.m.-2:55 p.m.

2 stops55h 55m

Simpson Bay Princess Juliana

Wed 29/4

1:35 p.m.-8:17 p.m.

2 stops31h 42m

C$ 1,890

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Winnipeg to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Winnipeg to Simpson Bay flights?

You could potentially save up to 27% on your flight if you consider stops on a Winnipeg to Simpson Bay flight.

When to book flights from Winnipeg to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Simpson Bay (YWG to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Simpson Bay

Fastest flight time

26h 48m

Direct flights

None
The fastest flight from Winnipeg to Simpson Bay takes 26h 48m
There are no direct flights from Winnipeg to Simpson Bay. There are no popular flight routes from Winnipeg to Simpson Bay.
Search flight deals

  • How far is Winnipeg to Simpson Bay Princess Juliana by plane?

    There are 4653.2 km between Winnipeg and Simpson Bay Princess Juliana. In terms of flight time, this usually takes a little over 26h 48m.

  • When did momondo last update prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

    Prices for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport are updated daily.

  • How many operators does momondo search for flights from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

  • How old do you have to be to fly from Winnipeg Airport to Simpson Bay Princess Juliana Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Winnipeg to Simpson Bay?

Best airlines flying from Winnipeg to Simpson Bay

Compare and see reviews for airlines that fly from Winnipeg to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 597Free CancellationRating
7.2
3,302 reviews
Search WestJet flights

Travelling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Simpson Bay?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to Simpson Bay. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to Simpson Bay with flexible booking policies on momondo?

Yes. All flights to Simpson Bay from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to Simpson Bay?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Simpson Bay from Winnipeg.

I’m not ready to book a flight from Winnipeg to Simpson Bay right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Winnipeg to Simpson Bay flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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WestJet