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Cheap flights from Calgary to Simpson Bay from C$ 265

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 20/6. 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 Calgary to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:25 p.m. - 2:20 p.m.
YYC
-
SXM
21h 55m
2 stops
WestJet Logo
3:20 p.m. - 10:10 a.m.
SXM
-
YYC
20h 50m
2 stops
C$ 611WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
2:25 p.m. - 2:20 p.m.
YYC
-
SXM
21h 55m
2 stops
WestJet Logo
3:20 p.m. - 11:20 a.m.
SXM
-
YYC
22h 00m
1 stop
C$ 622WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
8:40 p.m. - 2:20 p.m.
YYC
-
SXM
15h 40m
2 stops
WestJet Logo
3:20 p.m. - 12:44 a.m.
SXM
-
YYC
11h 24m
1 stop
C$ 623WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
3:20 p.m. - 2:20 p.m.
YYC
-
SXM
21h 00m
1 stop
WestJet Logo
3:20 p.m. - 12:44 a.m.
SXM
-
YYC
11h 24m
1 stop
C$ 629WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
7:10 p.m. - 2:20 p.m.
YYC
-
SXM
17h 10m
1 stop
WestJet Logo
3:20 p.m. - 8:35 a.m.
SXM
-
YYC
19h 15m
1 stop
C$ 630WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
8:40 p.m. - 2:20 p.m.
YYC
-
SXM
15h 40m
2 stops
WestJet Logo
3:20 p.m. - 10:10 a.m.
SXM
-
YYC
20h 50m
2 stops
C$ 643WestJet
Wed, 15 Jul - Sun, 19 Jul
WestJet Logo
7:10 p.m. - 2:20 p.m.
YYC
-
SXM
17h 10m
1 stop
WestJet Logo
3:20 p.m. - 1:10 p.m.
SXM
-
YYC
23h 50m
1 stop
C$ 668WestJet
Sun, 9 Aug - Thu, 13 Aug
WestJet Logo
11:45 p.m. - 2:20 p.m.
YYC
-
SXM
12h 35m
2 stops
WestJet Logo
3:20 p.m. - 8:00 a.m.
SXM
-
YYC
18h 40m
2 stops
C$ 670WestJet
Sun, 23 Aug - Thu, 27 Aug
WestJet Logo
7:10 p.m. - 2:20 p.m.
YYC
-
SXM
17h 10m
1 stop
WestJet Logo
3:20 p.m. - 8:35 a.m.
SXM
-
YYC
19h 15m
1 stop
C$ 671WestJet
Sun, 9 Aug - Thu, 13 Aug
United Airlines Logo
6:00 a.m. - 12:33 p.m.
YYC
-
SXM
52h 33m
2 stops
United Airlines Logo
3:50 p.m. - 9:48 p.m.
SXM
-
YYC
31h 58m
2 stops
C$ 743United Airlines
Sat, 23 May - Wed, 27 May

Air Canada flights from Calgary to Simpson Bay

Our best Air Canada deals on Calgary to Simpson Bay flight tickets
Air Canada
22 May
YYC7:20 a.m.Calgary
31h 40m
1 stop
SXM5:00 p.m.Simpson Bay Princess Juliana
30 May
SXM6:00 p.m.Simpson Bay Princess Juliana
19h 33m
1 stop
YYC11:33 a.m.Calgary
C$ 831
Air Canada
22 May
YYC8:30 p.m.Calgary
18h 30m
2 stops
SXM5:00 p.m.Simpson Bay Princess Juliana
30 May
SXM6:00 p.m.Simpson Bay Princess Juliana
19h 47m
2 stops
YYC11:47 a.m.Calgary
C$ 940
Air Canada
13 May
YYC7:45 p.m.Calgary
19h 15m
1 stop
SXM5:00 p.m.Simpson Bay Princess Juliana
16 May
SXM6:00 p.m.Simpson Bay Princess Juliana
18h 13m
1 stop
YYC10:13 a.m.Calgary
C$ 1,640

United Airlines flights from Calgary to Simpson Bay

Our best United Airlines deals on Calgary to Simpson Bay flight tickets
United Airlines
23 May
YYC6:00 a.m.Calgary
52h 33m
2 stops
SXM12:33 p.m.Simpson Bay Princess Juliana
27 May
SXM3:50 p.m.Simpson Bay Princess Juliana
31h 58m
2 stops
YYC9:48 p.m.Calgary
C$ 743
United Airlines
23 May
YYC1:27 p.m.Calgary
45h 06m
2 stops
SXM12:33 p.m.Simpson Bay Princess Juliana
26 May
SXM3:50 p.m.Simpson Bay Princess Juliana
31h 58m
2 stops
YYC9:48 p.m.Calgary
C$ 929
United Airlines
13 May
YYC6:00 a.m.Calgary
28h 33m
2 stops
SXM12:33 p.m.Simpson Bay Princess Juliana
16 May
SXM3:50 p.m.Simpson Bay Princess Juliana
31h 58m
2 stops
YYC9:48 p.m.Calgary
C$ 944

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 1 May 2026.
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

Cheapest round-trip

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

2:25 p.m.-2:20 p.m.

2 stops21h 55m

Simpson Bay Princess Juliana

Sun 19/7

3:20 p.m.-10:10 a.m.

2 stops20h 50m

C$ 611

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

2:25 p.m.-2:20 p.m.

2 stops21h 55m

Simpson Bay Princess Juliana

Sun 19/7

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

1 stop22h 00m

C$ 622
Quickest round-trip

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

8:40 p.m.-2:20 p.m.

2 stops15h 40m

Simpson Bay Princess Juliana

Sun 19/7

3:20 p.m.-12:44 a.m.

1 stop11h 24m

C$ 623

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

3:20 p.m.-2:20 p.m.

1 stop21h 00m

Simpson Bay Princess Juliana

Sun 19/7

3:20 p.m.-12:44 a.m.

1 stop11h 24m

C$ 629

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

7:10 p.m.-2:20 p.m.

1 stop17h 10m

Simpson Bay Princess Juliana

Sun 19/7

3:20 p.m.-8:35 a.m.

1 stop19h 15m

C$ 630

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 15/7

8:40 p.m.-2:20 p.m.

2 stops15h 40m

Simpson Bay Princess Juliana

Sun 19/7

3:20 p.m.-10:10 a.m.

2 stops20h 50m

C$ 642

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sun 9/8

7:10 p.m.-2:20 p.m.

1 stop17h 10m

Simpson Bay Princess Juliana

Thu 13/8

3:20 p.m.-1:10 p.m.

1 stop23h 50m

C$ 668

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sun 23/8

11:45 p.m.-2:20 p.m.

2 stops12h 35m

Simpson Bay Princess Juliana

Thu 27/8

3:20 p.m.-8:00 a.m.

2 stops18h 40m

C$ 670

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sun 9/8

7:10 p.m.-2:20 p.m.

1 stop17h 10m

Simpson Bay Princess Juliana

Thu 13/8

3:20 p.m.-8:35 a.m.

1 stop19h 15m

C$ 671

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 23/5

6:00 a.m.-12:33 p.m.

2 stops52h 33m

Simpson Bay Princess Juliana

Wed 27/5

3:50 p.m.-9:48 p.m.

2 stops31h 58m

C$ 743

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 typical price of a round-trip flight between Calgary and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, October 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$ 0. If you don’t want to visit Simpson Bay in October, then you should wait until September to fly from Calgary, when ticket prices are also cheap, with an average price of C$ 569.

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

You could potentially save up to 65% on your flight if you consider stops on a Calgary to Simpson Bay flight.

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

Fastest flight time

25h 30m

Direct flights

None
The fastest flight from Calgary to Simpson Bay takes 25h 30m
There are no direct flights from Calgary to Simpson Bay. There are no popular flight routes from Calgary to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Calgary to Simpson Bay

  • 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 25h 30m.

  • 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$ 416Free CancellationRating
7.2
3,331 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 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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WestJet