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Cheap flights from Calgary to Simpson Bay from C$ 651

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 18/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — SXM
26 Aug — 2 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Calgary to Simpson Bay

Enter your travel dates to find the best prices.

Cheapest flights from Calgary to Simpson Bay
Explore the most affordable flight options available from Calgary to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 July 2026.

Mon 23/1112:15 p.m.
YYC
-
SXM
2 stops24h 06m
WestJet
Mon 7/124:20 p.m.
SXM
-
YYC
2 stops18h 33m
WestJet
Deal found 26/7C$ 651
Wed 18/118:45 a.m.
YYC
-
SXM
2 stops27h 36m
WestJet
Wed 2/124:20 p.m.
SXM
-
YYC
2 stops18h 25m
WestJet
Deal found 23/7C$ 700
Wed 14/1011:25 a.m.
YYC
-
SXM
2 stops24h 45m
WestJet
Tue 13/43:20 p.m.
SXM
-
YYC
2 stops24h 40m
WestJet
Deal found 23/7C$ 726
Sat 22/81:00 a.m.
YYC
-
SXM
1 stop11h 20m
WestJet
Sun 30/83:20 p.m.
SXM
-
YYC
1 stop33h 00m
WestJet
Deal found 26/7C$ 745

Find flight deals from Calgary to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 27 July 2026.

Round-trip from

C$ 651

Popular in

May

Cheapest in

October

Average price

C$ 720
WestJet
  • WestJet
  • 23/11-7/12
  • 4 total stops
  • 42h 39m total
  • Calgary to Simpson Bay
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 140 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 27 July 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
Quickest round-trip

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 18/11

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

2 stops14h 31m

Simpson Bay Princess Juliana

Wed 2/12

4:20 p.m.-8:45 a.m.

2 stops18h 25m

C$ 651

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Mon 23/11

6:35 p.m.-2:21 p.m.

1 stop17h 46m

Simpson Bay Princess Juliana

Mon 7/12

4:20 p.m.-2:30 p.m.

1 stop24h 10m

C$ 662

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Wed 14/10

11:25 a.m.-2:10 p.m.

2 stops24h 45m

Simpson Bay Princess Juliana

Tue 13/4

3:20 p.m.-2:00 p.m.

2 stops24h 40m

C$ 726

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 22/8

1:00 a.m.-2:20 p.m.

1 stop11h 20m

Simpson Bay Princess Juliana

Sun 30/8

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

1 stop33h 00m

C$ 745

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Mon 18/1

6:30 a.m.-11:58 a.m.

2 stops27h 28m

Simpson Bay Princess Juliana

Wed 3/2

5:33 p.m.-1:48 p.m.

2 stops22h 15m

C$ 798

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Mon 18/1

1:40 p.m.-2:21 p.m.

2 stops46h 41m

Simpson Bay Princess Juliana

Wed 3/2

4:20 p.m.-12:15 p.m.

1 stop21h 55m

C$ 820

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/7

Sorted by cheapest first

Best time to book a flight from Calgary to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Calgary to Simpson Bay

What is the cheapest month to book a flight from Calgary to Simpson Bay?

Currently, October is the cheapest month in which you can book a flight from Calgary to Simpson Bay (average of C$ 697). Flying from Calgary to Simpson Bay in May is currently the most expensive (average of C$ 1,371). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Calgary to Simpson Bay?

Airfare is below average for this route at the moment.

Calgary to Simpson Bay flights typically cost between C$ 685 and C$ 857 in November.
The cheapest round-trip price found within the last 5 days was C$ 651 on WestJet (23 Nov-7 Dec).

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated 27 July 2026.
Read reviews from past customers who have flown WestJet from Calgary to Simpson Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,415 reviews
Check prices

Boarding

7.4

Food

6.2

Overall

7.2

Crew

7.9

Entertainment

6.1

Comfort

7.0

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,415 reviews
WestJet
7.2
Good
3,415 reviews
Check prices

Boarding

7.4

Food

6.2

Overall

7.2

Crew

7.9

Entertainment

6.1

Comfort

7.0

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

Related info for your journey

Find useful and relevant information for your journey from Calgary to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Calgary to Simpson Bay?

    For as low as C$ 662, WestJet can have you in Simpson Bay from Calgary in 17h 46m. The distance from Calgary to Simpson Bay is about 5765 km.

  • What is the cheapest airline to fly from Calgary to Simpson Bay round-trip?

    According to our current data, WestJet (C$ 582), offers the cheapest pricing from Calgary to Simpson Bay. This flight start at 37% lower than the current average price 3 months from now.

  • Can I find deals for flights from Calgary to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Calgary to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Simpson Bay.

  • Can I find deals for business class flights from Calgary to Simpson Bay?

    Yes. Cheapflights offers flight deals from Calgary to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Calgary to Simpson Bay?

    Currently, October is the cheapest month in which you can book a flight from Calgary to Simpson Bay (average of C$ 697). Flying from Calgary to Simpson Bay in May is currently the most expensive (average of C$ 1,371). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Simpson Bay?

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

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top airline flying from Calgary to Simpson Bay

Discover the top airline that operate flights from Calgary to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 27 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 582AverageC$ 796FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Calgary to Simpson Bay?

Cheapflights makes it easy to find Calgary to Simpson Bay flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Calgary to Simpson Bay?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Calgary to Simpson Bay for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Calgary to Simpson Bay with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Calgary to Simpson Bay flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Calgary to Simpson Bay become cheaper?

Of course! You can now track prices for flights from Calgary to Simpson Bay and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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