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Cheap flights from Winnipeg to Simpson Bay from C$ 236

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 31/1. 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
5:00 a.m. - 3:21 p.m.
YWG
-
SXM
8h 21m1 stop
WestJet Logo
4:20 p.m. - 7:12 p.m.
SXM
-
YWG
28h 52m1 stop
C$ 624WestJet
Mon, 12 Jan - Thu, 15 Jan
WestJet Logo
12:40 p.m. - 3:21 p.m.
YWG
-
SXM
24h 41m2 stops
WestJet Logo
4:20 p.m. - 11:53 a.m.
SXM
-
YWG
21h 33m2 stops
C$ 650WestJet
Mon, 12 Jan - Thu, 15 Jan
Multiple Airlines Logo
8:05 p.m. - 3:17 p.m.
YWG
-
SXM
17h 12m1 stop
Multiple Airlines Logo
2:15 p.m. - 3:09 p.m.
SXM
-
YWG
25h 54m2 stops
C$ 758Multiple Airlines
Tue, 17 Feb - Tue, 24 Mar
Multiple Airlines Logo
4:10 p.m. - 3:17 p.m.
YWG
-
SXM
21h 07m2 stops
Multiple Airlines Logo
2:15 p.m. - 10:15 a.m.
SXM
-
YWG
21h 00m2 stops
C$ 807Multiple Airlines
Tue, 17 Feb - Tue, 24 Mar
Multiple Airlines Logo
4:10 p.m. - 3:17 p.m.
YWG
-
SXM
21h 07m2 stops
Multiple Airlines Logo
2:15 p.m. - 6:05 p.m.
SXM
-
YWG
28h 50m3 stops
C$ 814Multiple Airlines
Tue, 17 Feb - Tue, 24 Mar
Multiple Airlines Logo
12:10 p.m. - 2:15 p.m.
YWG
-
SXM
24h 05m3 stops
Multiple Airlines Logo
2:15 p.m. - 6:05 p.m.
SXM
-
YWG
28h 50m3 stops
C$ 886Multiple Airlines
Tue, 17 Feb - Tue, 24 Mar
Air Canada Logo
6:00 a.m. - 1:40 p.m.
YWG
-
SXM
30h 40m2 stops
Air Canada Logo
2:40 p.m. - 12:32 p.m.
SXM
-
YWG
22h 52m2 stops
C$ 1,011Air Canada
Sat, 21 Mar - Sat, 4 Apr
WestJet Logo
8:05 p.m. - 3:17 p.m.
YWG
-
SXM
17h 12m1 stop
WestJet Logo
3:20 p.m. - 11:32 a.m.
SXM
-
YWG
21h 12m1 stop
C$ 1,020WestJet
Tue, 17 Feb - Tue, 24 Mar
Air Canada Logo
6:00 a.m. - 1:40 p.m.
YWG
-
SXM
30h 40m2 stops
Air Canada Logo
2:40 p.m. - 10:07 a.m.
SXM
-
YWG
20h 27m1 stop
C$ 1,123Air Canada
Sat, 21 Mar - Sat, 4 Apr
Air Canada Logo
1:45 p.m. - 1:40 p.m.
YWG
-
SXM
22h 55m1 stop
Air Canada Logo
2:40 p.m. - 10:07 a.m.
SXM
-
YWG
20h 27m1 stop
C$ 1,363Air Canada
Sat, 21 Mar - Sat, 4 Apr

WestJet flights from Winnipeg to Simpson Bay

Our best WestJet deals on Winnipeg to Simpson Bay flight tickets
WestJet
23 Jan
YWG5:00 a.m.Winnipeg
8h 21m
1 stop
SXM3:21 p.m.Simpson Bay Princess Juliana
27 Jan
SXM4:20 p.m.Simpson Bay Princess Juliana
29h 46m
2 stops
YWG8:06 p.m.Winnipeg
C$ 557
Find similar
WestJet
23 Jan
YWG5:00 a.m.Winnipeg
8h 21m
1 stop
SXM3:21 p.m.Simpson Bay Princess Juliana
27 Jan
SXM4:20 p.m.Simpson Bay Princess Juliana
21h 15m
1 stop
YWG11:35 a.m.Winnipeg
C$ 566
Find similar
WestJet
12 Jan
YWG5:00 a.m.Winnipeg
8h 21m
1 stop
SXM3:21 p.m.Simpson Bay Princess Juliana
15 Jan
SXM4:20 p.m.Simpson Bay Princess Juliana
34h 21m
2 stops
YWG12:41 a.m.Winnipeg
C$ 601
Find similar

Air Canada flights from Winnipeg to Simpson Bay

Our best Air Canada deals on Winnipeg to Simpson Bay flight tickets
Air Canada
21 Mar
YWG6:00 a.m.Winnipeg
30h 40m
2 stops
SXM1:40 p.m.Simpson Bay Princess Juliana
4 Apr
SXM2:40 p.m.Simpson Bay Princess Juliana
22h 52m
2 stops
YWG12:32 p.m.Winnipeg
C$ 1,011
Find similar
Air Canada
21 Mar
YWG6:00 a.m.Winnipeg
30h 40m
2 stops
SXM1:40 p.m.Simpson Bay Princess Juliana
4 Apr
SXM2:40 p.m.Simpson Bay Princess Juliana
20h 27m
1 stop
YWG10:07 a.m.Winnipeg
C$ 1,123
Find similar
Air Canada
21 Mar
YWG1:45 p.m.Winnipeg
22h 55m
1 stop
SXM1:40 p.m.Simpson Bay Princess Juliana
4 Apr
SXM2:40 p.m.Simpson Bay Princess Juliana
20h 27m
1 stop
YWG10:07 a.m.Winnipeg
C$ 1,363
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 18 December 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

Mon 12/1

5:00 a.m.-3:21 p.m.

1 stop8h 21m

Simpson Bay Princess Juliana

Thu 15/1

4:20 p.m.-7:12 p.m.

1 stop28h 52m

C$ 624

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Mon 12/1

12:40 p.m.-3:21 p.m.

2 stops24h 41m

Simpson Bay Princess Juliana

Thu 15/1

4:20 p.m.-11:53 a.m.

2 stops21h 33m

C$ 650

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 17/2

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

1 stop17h 12m

Simpson Bay Princess Juliana

Tue 24/3

2:15 p.m.-3:09 p.m.

2 stops25h 54m

C$ 758

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 17/2

4:10 p.m.-3:17 p.m.

2 stops21h 07m

Simpson Bay Princess Juliana

Tue 24/3

2:15 p.m.-10:15 a.m.

2 stops21h 00m

C$ 807

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 17/2

4:10 p.m.-3:17 p.m.

2 stops21h 07m

Simpson Bay Princess Juliana

Tue 24/3

2:15 p.m.-6:05 p.m.

3 stops28h 50m

C$ 814

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 17/2

12:10 p.m.-2:15 p.m.

3 stops24h 05m

Simpson Bay Princess Juliana

Tue 24/3

2:15 p.m.-6:05 p.m.

3 stops28h 50m

C$ 886

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 21/3

6:00 a.m.-1:40 p.m.

2 stops30h 40m

Simpson Bay Princess Juliana

Sat 4/4

2:40 p.m.-12:32 p.m.

2 stops22h 52m

C$ 1,011

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Tue 17/2

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

1 stop17h 12m

Simpson Bay Princess Juliana

Tue 24/3

3:20 p.m.-11:32 a.m.

1 stop21h 12m

C$ 1,020

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 21/3

6:00 a.m.-1:40 p.m.

2 stops30h 40m

Simpson Bay Princess Juliana

Sat 4/4

2:40 p.m.-10:07 a.m.

1 stop20h 27m

C$ 1,123

WinnipegSimpson Bay

YWG - SXM

YWGSXM

Winnipeg

Sat 21/3

1:45 p.m.-1:40 p.m.

1 stop22h 55m

Simpson Bay Princess Juliana

Sat 4/4

2:40 p.m.-10:07 a.m.

1 stop20h 27m

C$ 1,363

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$ 756. 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$ 1,469.

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$ 660 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$ 1,172.

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

You could potentially save up to 31% 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

17h 12m

Direct flights

None
The fastest flight from Winnipeg to Simpson Bay takes 17h 12m
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$ 562Free CancellationRating
7.2
3,204 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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