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Cheap flights from Calgary to Simpson Bay from C$ 310

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Simpson Bay departing on 11/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Calgary to Simpson Bay

Cheap round-trip flights

WestJet Logo
9:50 p.m. - 2:21 p.m.YYC-SXM
14h 31m2 stops
WestJet Logo
4:20 p.m. - 6:57 a.m.SXM-YYC
17h 37m2 stops
C$ 490WestJet
Find Deal
Thu, 30 Oct - Thu, 6 Nov
WestJet Logo
12:15 a.m. - 2:21 p.m.YYC-SXM
12h 06m1 stop
WestJet Logo
4:20 p.m. - 10:20 a.m.SXM-YYC
21h 00m1 stop
C$ 492WestJet
Find Deal
Wed, 29 Oct - Thu, 6 Nov
American Airlines Logo
6:29 a.m. - 1:19 p.m.YYC-SXM
28h 50m2 stops
American Airlines Logo
2:20 p.m. - 12:05 p.m.SXM-YYC
23h 45m2 stops
C$ 747American Airlines
Find Deal
Sun, 7 Sep - Sun, 21 Sep
Logo
11:05 a.m. - 2:00 p.m.YYC-SXM
24h 55m2 stops
Logo
12:25 p.m. - 8:10 a.m.SXM-YYC
21h 45m2 stops
C$ 759
Find Deal
Sun, 7 Sep - Sun, 21 Sep
American Airlines Logo
1:29 p.m. - 1:25 p.m.YYC-SXM
21h 56m2 stops
American Airlines Logo
4:30 p.m. - 9:58 p.m.SXM-YYC
31h 28m2 stops
C$ 772American Airlines
Find Deal
Fri, 22 Aug - Fri, 29 Aug
Logo
12:20 a.m. - 1:14 p.m.YYC-SXM
10h 54m1 stop
Logo
12:25 p.m. - 3:40 p.m.SXM-YYC
29h 15m3 stops
C$ 838
Find Deal
Sat, 6 Sep - Sun, 21 Sep
Delta Logo
7:40 p.m. - 2:02 p.m.YYC-SXM
15h 22m2 stops
Delta Logo
5:20 p.m. - 5:50 p.m.SXM-YYC
27h 30m2 stops
C$ 1,253Delta
Find Deal
Fri, 12 Dec - Sat, 27 Dec
Delta Logo
2:35 p.m. - 2:35 p.m.YYC-SXM
21h 00m2 stops
Delta Logo
5:20 p.m. - 5:50 p.m.SXM-YYC
27h 30m2 stops
C$ 1,289Delta
Find Deal
Fri, 12 Dec - Sat, 27 Dec
Air Transat Logo
7:10 a.m. - 11:55 a.m.YYC-SXM
25h 45m1 stop
Air Transat Logo
1:25 p.m. - 3:32 p.m.SXM-YYC
29h 07m1 stop
C$ 2,585Air Transat
Find Deal
Fri, 12 Dec - Sat, 27 Dec
Air Transat Logo
7:10 a.m. - 11:55 a.m.YYC-SXM
25h 45m1 stop
Air Transat Logo
1:25 p.m. - 3:32 p.m.SXM-YYC
29h 07m1 stop
C$ 2,600Air Transat
Find Deal
Fri, 12 Dec - Sat, 27 Dec

American Airlines flights from Calgary to Simpson Bay

Our best American Airlines deals on Calgary to Simpson Bay flight tickets
American Airlines
7 Sep
YYC6:29 a.m.Calgary
28h 50m
2 stops
SXM1:19 p.m.Simpson Bay Princess Juliana
21 Sep
SXM2:20 p.m.Simpson Bay Princess Juliana
23h 45m
2 stops
YYC12:05 p.m.Calgary
C$ 747
Find similar
American Airlines
22 Aug
YYC1:29 p.m.Calgary
21h 56m
2 stops
SXM1:25 p.m.Simpson Bay Princess Juliana
29 Aug
SXM4:30 p.m.Simpson Bay Princess Juliana
31h 28m
2 stops
YYC9:58 p.m.Calgary
C$ 772
Find similar
American Airlines
24 Sep
YYC6:45 a.m.Calgary
28h 34m
2 stops
SXM1:19 p.m.Simpson Bay Princess Juliana
1 Oct
SXM2:20 p.m.Simpson Bay Princess Juliana
23h 31m
2 stops
YYC11:51 a.m.Calgary
C$ 883
Find similar

WestJet flights from Calgary to Simpson Bay

Our best WestJet deals on Calgary to Simpson Bay flight tickets
WestJet
30 Oct
YYC9:50 p.m.Calgary
14h 31m
2 stops
SXM2:21 p.m.Simpson Bay Princess Juliana
6 Nov
SXM4:20 p.m.Simpson Bay Princess Juliana
17h 37m
2 stops
YYC6:57 a.m.Calgary
C$ 490
Find similar
WestJet
29 Oct
YYC12:15 a.m.Calgary
12h 06m
1 stop
SXM2:21 p.m.Simpson Bay Princess Juliana
6 Nov
SXM4:20 p.m.Simpson Bay Princess Juliana
21h 00m
1 stop
YYC10:20 a.m.Calgary
C$ 492
Find similar
WestJet
29 Oct
YYC12:15 a.m.Calgary
12h 06m
1 stop
SXM2:21 p.m.Simpson Bay Princess Juliana
6 Nov
SXM4:20 p.m.Simpson Bay Princess Juliana
24h 40m
2 stops
YYC2:00 p.m.Calgary
C$ 494
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Calgary 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 30 July 2025.
Use the filters below to find and compare flights from Calgary to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Thu 30/10

9:50 p.m.-2:21 p.m.

2 stops14h 31m

Simpson Bay Princess Juliana

Thu 6/11

4:20 p.m.-6:57 a.m.

2 stops17h 37m

C$ 490

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 29/10

12:15 a.m.-2:21 p.m.

1 stop12h 06m

Simpson Bay Princess Juliana

Thu 6/11

4:20 p.m.-10:20 a.m.

1 stop21h 00m

C$ 492

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sun 7/9

6:29 a.m.-1:19 p.m.

2 stops28h 50m

Simpson Bay Princess Juliana

Sun 21/9

2:20 p.m.-12:05 p.m.

2 stops23h 45m

C$ 747

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sun 7/9

11:05 a.m.-2:00 p.m.

2 stops24h 55m

Simpson Bay Princess Juliana

Sun 21/9

12:25 p.m.-8:10 a.m.

2 stops21h 45m

C$ 759

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 22/8

1:29 p.m.-1:25 p.m.

2 stops21h 56m

Simpson Bay Princess Juliana

Fri 29/8

4:30 p.m.-9:58 p.m.

2 stops31h 28m

C$ 772

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 6/9

12:20 a.m.-1:14 p.m.

1 stop10h 54m

Simpson Bay Princess Juliana

Sun 21/9

12:25 p.m.-3:40 p.m.

3 stops29h 15m

C$ 838

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

7:40 p.m.-2:02 p.m.

2 stops15h 22m

Simpson Bay Princess Juliana

Sat 27/12

5:20 p.m.-5:50 p.m.

2 stops27h 30m

C$ 1,253

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

2:35 p.m.-2:35 p.m.

2 stops21h 00m

Simpson Bay Princess Juliana

Sat 27/12

5:20 p.m.-5:50 p.m.

2 stops27h 30m

C$ 1,289

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

7:10 a.m.-11:55 a.m.

1 stop25h 45m

Simpson Bay Princess Juliana

Sat 27/12

1:25 p.m.-3:32 p.m.

1 stop29h 07m

C$ 2,585

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

7:10 a.m.-11:55 a.m.

1 stop25h 45m

Simpson Bay Princess Juliana

Sat 27/12

1:25 p.m.-3:32 p.m.

1 stop29h 07m

C$ 2,600

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Calgary 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 month to fly to Simpson Bay?

In general, April is the cheapest month to fly from Calgary to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 671. If you don’t want to visit Simpson Bay in April, then you should wait until August to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 671.

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 Monday when prices can be found for as low as C$ 743. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Calgary because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 1,038.

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

Flying to Simpson Bay from Calgary in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 739 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around C$ 977.

When to book flights from Calgary to Simpson Bay

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

Cheap Calgary to Simpson Bay (YYC to SXM) flight deals and tips

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

Best price found

C$ 310

Fastest flight time

10h 14m

Direct flights

None

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Calgary in the past 72 hours is C$ 310. The best round-trip flight deal from Calgary to Simpson Bay found on momondo in the last 72 hours is C$ 490.
The fastest flight from Calgary to Simpson Bay takes 10h 14m
There are no direct flights from Calgary to Simpson Bay. Popular non-direct route for this connection is Calgary Airport - Simpson Bay Princess Juliana Airport.
There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)
Search flight deals

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

    A flight from Calgary to Simpson Bay Princess Juliana will travel around 5764.2 km. By plane, this route typically takes 10h 14m.

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

    Prices for flights from Calgary Airport to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Calgary 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 Calgary 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 required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Calgary to Simpson Bay

Compare and see reviews for airlines that fly from Calgary to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 483Free CancellationRating
7.2
2,975 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 713Free CancellationRating
7.1
9,837 reviews
Search Air Canada 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 Calgary to Simpson Bay?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Simpson Bay from Calgary.

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

Yes. momondo allows you to filter the results for Calgary to Simpson Bay flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Simpson Bay from Calgary. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Simpson Bay from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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