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Cheap flights from Calgary to Simpson Bay from C$ 309

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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — SXM
3 Aug — 10 Aug1
1 adult

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 29 July 2025.

Round-trip from

C$ 668

One-way from

C$ 309

Popular in

February

Cheapest in

April

Average price

C$ 846
WestJet
  • WestJet
  • 6/9-21/9
  • 3 total stops
  • 35h 02m total
  • Calgary to Simpson Bay
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American Airlines
  • American Airlines
  • 11/9
  • 2 total stops
  • 28h 34m total
  • Calgary to Simpson Bay
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 151 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 36 potential savings vs. average RT price).
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Average for round-trip flights in July 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 29 July 2025.

Thu 30/109:50 p.m.YYC - SXM
2 stops14h 31mWestJet
Thu 6/114:20 p.m.SXM - YYC
2 stops17h 37mWestJet
Deal found 28/7C$ 488
Sun 7/911:05 a.m.YYC - SXM
2 stops24h 55mMultiple Airlines
Sun 21/912:25 p.m.SXM - YYC
2 stops21h 45mMultiple Airlines
Deal found 29/7C$ 757
Fri 22/81:29 p.m.YYC - SXM
2 stops21h 56mAmerican Airlines
Fri 29/84:30 p.m.SXM - YYC
2 stops31h 28mAmerican Airlines
Deal found 27/7C$ 770
Fri 12/127:40 p.m.YYC - SXM
2 stops15h 22mDelta
Sat 27/125:20 p.m.SXM - YYC
2 stops27h 30mDelta
Deal found 29/7C$ 1,250
Fri 12/127:10 a.m.YYC - SXM
1 stop25h 45mAir Transat
Sat 27/121:25 p.m.SXM - YYC
1 stop29h 07mAir Transat
Deal found 29/7C$ 2,578
Tue 29/72:00 p.m.YYC - SXM
2 stops44h 29mAir Canada
Tue 5/81:35 p.m.SXM - YYC
1 stop30h 21mAir Canada
Deal found 28/7C$ 3,384

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 29 July 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

Sat 6/9

1:00 a.m.-1:14 p.m.

1 stop10h 14m

Simpson Bay Princess Juliana

Sun 21/9

2:10 p.m.-12:58 p.m.

2 stops24h 48m

C$ 668

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$ 757

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$ 770

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Thu 11/9

6:45 a.m.-1:19 p.m.

2 stops28h 34m

C$ 309

CalgarySimpson Bay

YYC - SXM

YYCSXM

Calgary

Thu 11/9

6:20 a.m.-2:00 p.m.

3 stops29h 40m

C$ 387

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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$ 600). 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 29 July 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.

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 29 July 2025.
Read reviews from past customers who have flown American Airlines and 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.
American Airlines
7.2
Good
10,000 reviews
Check prices

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2023

LHR - JFK

Good flight. Only thing is that the seatbelt sign was on all the time, though some people got up anyway and it seemed fine to the crew, and other times an announcement was made to not get up and to fasten seat belt. Just a little confusing to know if I could get up…but all was well.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews
Check prices

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2023

LHR - JFK

Good flight. Only thing is that the seatbelt sign was on all the time, though some people got up anyway and it seemed fine to the crew, and other times an announcement was made to not get up and to fasten seat belt. Just a little confusing to know if I could get up…but all was well.
WestJet
7.2
Good
2,973 reviews
American Airlines
7.2
Good
10,000 reviews
Check prices

Comfort

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Overall

7.2

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2023

LHR - JFK

Good flight. Only thing is that the seatbelt sign was on all the time, though some people got up anyway and it seemed fine to the crew, and other times an announcement was made to not get up and to fasten seat belt. Just a little confusing to know if I could get up…but all was well.

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.

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

    According to our current data, WestJet (C$ 668), and American Airlines (C$ 770) offers the cheapest pricing from Calgary to Simpson Bay. These flights start at 24% 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$ 600). 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

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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 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 29 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 481AverageC$ 934FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 711AverageC$ 1,260FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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?

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

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