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Cheap flights from Winnipeg to Simpson Bay from C$ 294

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Simpson Bay departing on 30/10. 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

Multiple Airlines Logo
12:10 p.m. - 3:17 p.m.YWG-SXM
25h 07m1 stop
Multiple Airlines Logo
4:28 p.m. - 3:09 p.m.SXM-YWG
24h 41m2 stops
C$ 886Multiple Airlines
Find Deal
Sun, 1 Feb - Sat, 28 Feb
WestJet Logo
3:15 p.m. - 1:14 p.m.YWG-SXM
20h 59m2 stops
WestJet Logo
3:20 p.m. - 3:21 p.m.SXM-YWG
25h 01m2 stops
C$ 1,025WestJet
Find Deal
Sat, 11 Oct - Sun, 26 Oct
WestJet Logo
3:15 p.m. - 1:14 p.m.YWG-SXM
20h 59m2 stops
WestJet Logo
3:20 p.m. - 7:12 p.m.SXM-YWG
28h 52m1 stop
C$ 1,037WestJet
Find Deal
Sat, 11 Oct - Sun, 26 Oct
WestJet Logo
2:35 p.m. - 1:14 p.m.YWG-SXM
21h 39m1 stop
WestJet Logo
3:20 p.m. - 11:35 a.m.SXM-YWG
21h 15m1 stop
C$ 1,041WestJet
Find Deal
Sat, 11 Oct - Sun, 26 Oct
Multiple Airlines Logo
8:05 p.m. - 3:17 p.m.YWG-SXM
17h 12m1 stop
Multiple Airlines Logo
1:25 p.m. - 11:35 p.m.SXM-YWG
12h 10m1 stop
C$ 1,052Multiple Airlines
Find Deal
Sun, 1 Feb - Sat, 28 Feb
Multiple Airlines Logo
5:15 p.m. - 7:30 p.m.YWG-SXM
25h 15m3 stops
Multiple Airlines Logo
3:20 p.m. - 10:08 a.m.SXM-YWG
19h 48m2 stops
C$ 1,105Multiple Airlines
Find Deal
Sat, 11 Oct - Sun, 26 Oct
Multiple Airlines Logo
6:15 a.m. - 3:17 p.m.YWG-SXM
31h 02m2 stops
Multiple Airlines Logo
5:00 p.m. - 12:39 a.m.SXM-YWG
33h 39m2 stops
C$ 1,337Multiple Airlines
Find Deal
Sun, 1 Feb - Sat, 28 Feb
Delta Logo
7:30 a.m. - 12:18 p.m.YWG-SXM
26h 48m2 stops
Delta Logo
1:50 p.m. - 11:54 a.m.SXM-YWG
24h 04m2 stops
C$ 1,513Delta
Find Deal
Sun, 28 Dec - Fri, 2 Jan
Delta Logo
7:30 a.m. - 12:18 p.m.YWG-SXM
26h 48m2 stops
Delta Logo
1:50 p.m. - 11:54 a.m.SXM-YWG
24h 04m2 stops
C$ 1,519Delta
Find Deal
Sun, 28 Dec - Fri, 2 Jan
United Airlines Logo
8:40 a.m. - 1:50 p.m.YWG-SXM
51h 10m2 stops
United Airlines Logo
4:55 p.m. - 11:44 p.m.SXM-YWG
32h 49m2 stops
C$ 1,746United Airlines
Find Deal
Sun, 28 Dec - Fri, 2 Jan

Delta flights from Winnipeg to Simpson Bay

Our best Delta deals on Winnipeg to Simpson Bay flight tickets
Delta
28 Dec
YWG7:30 a.m.Winnipeg
26h 48m
2 stops
SXM12:18 p.m.Simpson Bay Princess Juliana
2 Jan
SXM1:50 p.m.Simpson Bay Princess Juliana
24h 04m
2 stops
YWG11:54 a.m.Winnipeg
C$ 1,513
Find similar
Delta
28 Dec
YWG7:30 a.m.Winnipeg
26h 48m
2 stops
SXM12:18 p.m.Simpson Bay Princess Juliana
2 Jan
SXM1:50 p.m.Simpson Bay Princess Juliana
24h 04m
2 stops
YWG11:54 a.m.Winnipeg
C$ 1,519
Find similar
Delta
28 Dec
YWG7:30 a.m.Winnipeg
29h 20m
1 stop
SXM2:50 p.m.Simpson Bay Princess Juliana
2 Jan
SXM1:50 p.m.Simpson Bay Princess Juliana
24h 04m
2 stops
YWG11:54 a.m.Winnipeg
C$ 1,819
Find similar

WestJet flights from Winnipeg to Simpson Bay

Our best WestJet deals on Winnipeg to Simpson Bay flight tickets
WestJet
11 Oct
YWG3:15 p.m.Winnipeg
20h 59m
2 stops
SXM1:14 p.m.Simpson Bay Princess Juliana
26 Oct
SXM3:20 p.m.Simpson Bay Princess Juliana
25h 01m
2 stops
YWG3:21 p.m.Winnipeg
C$ 1,025
Find similar
WestJet
11 Oct
YWG3:15 p.m.Winnipeg
20h 59m
2 stops
SXM1:14 p.m.Simpson Bay Princess Juliana
26 Oct
SXM3:20 p.m.Simpson Bay Princess Juliana
28h 52m
1 stop
YWG7:12 p.m.Winnipeg
C$ 1,037
Find similar
WestJet
11 Oct
YWG2:35 p.m.Winnipeg
21h 39m
1 stop
SXM1:14 p.m.Simpson Bay Princess Juliana
26 Oct
SXM3:20 p.m.Simpson Bay Princess Juliana
21h 15m
1 stop
YWG11:35 a.m.Winnipeg
C$ 1,041
Find similar

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 17 September 2025.
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

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 1/2

12:10 p.m.-3:17 p.m.

1 stop25h 07m

Simpson Bay Princess Juliana

Sat 28/2

4:28 p.m.-3:09 p.m.

2 stops24h 41m

C$ 886

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$ 1,025

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.-7:12 p.m.

1 stop28h 52m

C$ 1,037

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 11/10

2:35 p.m.-1:14 p.m.

1 stop21h 39m

Simpson Bay Princess Juliana

Sun 26/10

3:20 p.m.-11:35 a.m.

1 stop21h 15m

C$ 1,041

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 1/2

8:05 p.m.-3:17 p.m.

1 stop17h 12m

Simpson Bay Princess Juliana

Sat 28/2

1:25 p.m.-11:35 p.m.

1 stop12h 10m

C$ 1,052

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$ 1,105

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 1/2

6:15 a.m.-3:17 p.m.

2 stops31h 02m

Simpson Bay Princess Juliana

Sat 28/2

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

2 stops33h 39m

C$ 1,337

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:30 a.m.-12:18 p.m.

2 stops26h 48m

Simpson Bay Princess Juliana

Fri 2/1

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

2 stops24h 04m

C$ 1,513

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sun 28/12

7:30 a.m.-12:18 p.m.

2 stops26h 48m

Simpson Bay Princess Juliana

Fri 2/1

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

2 stops24h 04m

C$ 1,519

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$ 1,746

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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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

What is the cheapest day to depart on your flight to Simpson Bay?

The cheapest day to depart on your flight to Simpson Bay is on a Thursday when prices can be found for as low as C$ 755. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 1,467.

What is the cheapest time of day to depart on your flight to Simpson Bay?

Flying to Simpson Bay from Winnipeg in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as C$ 659 when looking at flights departing in the afternoon. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around C$ 1,170.

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

Direct flights

None
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 17h 12m.

  • 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$ 561Free CancellationRating
7.2
3,095 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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