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Cheap flights from Calgary to Simpson Bay from C$ 308

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — SXM
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap 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 11 September 2025.

Round-trip from

C$ 1,466

One-way from

C$ 308

Popular in

February

Cheapest in

April

Average price

C$ 694
Delta
  • Delta
  • 12/12-27/12
  • 4 total stops
  • 42h 50m total
  • Calgary to Simpson Bay
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United Airlines
  • United Airlines
  • 25/10
  • 2 total stops
  • 28h 03m total
  • Calgary to Simpson Bay
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 159 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Calgary to Simpson Bay

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 11 September 2025.

Fri 12/127:40 p.m.YYC - SXM
2 stops15h 20mDelta
Sat 27/125:20 p.m.SXM - YYC
2 stops27h 30mDelta
Deal found 11/9C$ 1,466
Fri 12/1212:40 p.m.YYC - SXM
1 stop20h 35mAir Transat
Sat 27/121:25 p.m.SXM - YYC
1 stop12h 57mAir Transat
Deal found 10/9C$ 2,088
Thu 11/1212:15 a.m.YYC - SXM
1 stop12h 06mMultiple Airlines
Sat 27/125:00 p.m.SXM - YYC
2 stops34h 44mMultiple Airlines
Deal found 11/9C$ 3,729

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 11 September 2025.
Use the filters below to find and compare flights from Calgary to Simpson Bay that are best for you.

Fly from

Calgary

Fly to

Simpson Bay

Route

Depart

Return

Price

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

7:40 p.m.-2:00 p.m.

2 stops15h 20m

Simpson Bay Princess Juliana

Sat 27/12

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

2 stops27h 30m

C$ 1,466

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 12/12

12:40 p.m.-12:15 p.m.

1 stop20h 35m

Simpson Bay Princess Juliana

Sat 27/12

1:25 p.m.-11:22 p.m.

1 stop12h 57m

C$ 2,088

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Thu 11/12

12:15 a.m.-3:21 p.m.

1 stop12h 06m

Simpson Bay Princess Juliana

Sat 27/12

5:00 p.m.-12:44 a.m.

2 stops34h 44m

C$ 3,729

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 25/10

6:15 a.m.-12:18 p.m.

2 stops28h 03m

C$ 308

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Fri 24/10

12:20 a.m.-11:31 a.m.

2 stops33h 11m

C$ 352

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Sat 25/10

7:15 a.m.-12:18 p.m.

1 stop27h 03m

C$ 406

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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, September is the cheapest month in which you can book a flight from Calgary to Simpson Bay (average of C$ 324). Flying from Calgary to Simpson Bay in February is currently the most expensive (average of C$ 586). 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.

What is the cheapest time of day to fly from YYC to SXM?

Find hourly flight availability from Calgary to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 11 September 2025.

It’s optimal to fly from Calgary to Simpson Bay in the morning. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the afternoon.

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

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 11 September 2025.
Read reviews from past customers who have flown WestJet and Air Canada 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
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.
WestJet
7.2
Good
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.
Air Canada
7.1
Good
10,000 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2025

YYC - NRT

I like direct flight from Calgary to Japan. But it’s my fault, I did not decide my seat till last minute. I was in the middle seat in the middle lane, I hesitated asking to go to bathroom.

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$ 1,466, Delta can have you in Simpson Bay from Calgary in 15h 20m. The distance from Calgary to Simpson Bay is about 5765 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Calgary to Simpson Bay round-trip?

    According to our current data, WestJet (C$ 486), and Air Canada (C$ 718) offers the cheapest pricing from Calgary to Simpson Bay. These flights start at 45% 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, September is the cheapest month in which you can book a flight from Calgary to Simpson Bay (average of C$ 324). Flying from Calgary to Simpson Bay in February is currently the most expensive (average of C$ 586). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 2 airlines flying from Calgary to Simpson Bay

Discover the top 2 airlines 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 486AverageC$ 924FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 718AverageC$ 1,273FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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