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Cheap flights from Calgary to Simpson Bay from C$ 311

YYC — SXM
24 Nov — 1 Dec1
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

Sun 15/117:00 a.m. -
2 stops28h 50m
Thu 3/122:52 p.m. -
2 stops50h 29m
Deal found 22/10C$ 752
Thu 10/126:00 a.m. -
1 stop31h 25m
Tue 15/124:20 p.m. -
1 stop20h 45m
Deal found 21/10C$ 808
Sun 15/117:45 a.m. -
1 stop28h 05m
Sat 5/125:00 p.m. -
2 stops21h 35m
Deal found 22/10C$ 881
Thu 10/123:06 p.m. -
2 stops44h 44m
Tue 15/122:52 p.m. -
2 stops47h 43m
Deal found 21/10C$ 966
Wed 18/117:00 a.m. -
2 stops28h 50m
Sat 5/125:00 p.m. -
2 stops21h 35m
Deal found 22/10C$ 968
Tue 17/117:30 a.m. -
2 stops26h 25m
Fri 4/124:20 p.m. -
1 stop34h 25m
Deal found 22/10C$ 1,034
Tue 17/117:30 a.m. -
2 stops26h 25m
Thu 3/124:20 p.m. -
1 stop20h 20m
Deal found 22/10C$ 1,042
Sun 15/117:01 a.m. -
2 stops31h 30m
Tue 1/125:29 p.m. -
2 stops45h 42m
Deal found 22/10C$ 1,084
Sun 15/117:01 a.m. -
2 stops31h 30m
Mon 30/115:29 p.m. -
2 stops54h 08m
Deal found 22/10C$ 1,085
Tue 17/117:30 a.m. -
2 stops26h 25m
Wed 2/121:05 p.m. -
1 stop12h 50m
Deal found 22/10C$ 1,095

Find flight deals from Calgary to Simpson Bay

Round-trip from

C$ 738

One-way from

C$ 311

Popular in

March

Cheapest in

November

Average price

C$ 693
WestJet
  • WestJet
  • 18/1-28/1
  • 2 total stops
  • 45h 55m total
  • Calgary to Simpson Bay
Search Deals
WestJet
  • WestJet
  • 7/12-31/12
  • 1 total stop
  • 13h 20m total
  • Calgary to Simpson Bay
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 283 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 70 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

Cheapflights Fare Finder

 
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 Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Sat 5/12

7:00 a.m.-1:50 p.m.

2 stops28h 50m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 366

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Tue 8/12

7:00 a.m.-1:32 p.m.

2 stops28h 32m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 375

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Wed 9/12

7:00 a.m.-4:26 p.m.

2 stops31h 26m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 389

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Wed 9/12

3:00 p.m.-3:25 p.m.

1 stop22h 25m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 429

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Tue 8/12

7:00 a.m.-1:50 p.m.

3 stops28h 50m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 506
Quickest round-trip

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Sat 5/12

5:15 p.m.-3:25 p.m.

3 stops20h 10m

Simpson Bay Princess Juliana

Wed 31/12

12:00 a.m.-9:00 p.m.

Nonstop0h 00m

C$ 569

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Sun 17/1

12:05 a.m.-3:25 p.m.

1 stop13h 20m

Simpson Bay Princess Juliana

Wed 3/2

4:20 p.m.-11:05 a.m.

1 stop20h 45m

C$ 741

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Mon 16/11

7:00 a.m.-1:50 p.m.

2 stops28h 50m

Simpson Bay Princess Juliana

Sat 5/12

5:00 p.m.-12:35 p.m.

2 stops21h 35m

C$ 752

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Mon 16/11

7:00 a.m.-1:50 p.m.

2 stops28h 50m

Simpson Bay Princess Juliana

Wed 2/12

2:52 p.m.-12:35 p.m.

2 stops47h 43m

C$ 752

CalgarySimpson Bay

YYC Calgary - SXM Simpson Bay Princess Juliana

YYCSXM

Calgary

Mon 18/1

3:06 p.m.-1:50 p.m.

2 stops44h 44m

Simpson Bay Princess Juliana

Wed 3/2

2:52 p.m.-12:35 p.m.

2 stops47h 43m

C$ 784

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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

Cheapflights Insights

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

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

Airfare is above average for this route at the moment.

Calgary to Simpson Bay flights typically cost between C$ 580 and C$ 691 in January.
The cheapest round-trip price found within the last 5 days was C$ 738 on WestJet (18 Jan-28 Jan).

Reviews of airlines servicing Simpson Bay

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
3,445 reviews
Check prices

Overall

7.2

Entertainment

6.1

Food

6.2

Comfort

7.1

Boarding

7.4

Crew

7.9

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
3,445 reviews
WestJet
7.2
Good
3,445 reviews
Check prices

Overall

7.2

Entertainment

6.1

Food

6.2

Comfort

7.1

Boarding

7.4

Crew

7.9

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

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

    For as low as C$ 741, WestJet can have you in Simpson Bay from Calgary in 13h 20m. The distance from Calgary to Simpson Bay is about 5765 km. This flight may include one or multiple stops.

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

    According to our current data, WestJet (C$ 492), offers the cheapest pricing from Calgary to Simpson Bay. This flight start at 42% 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.

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

Simpson Bay Princess Juliana Airport car rentals
Philipsburg car rentals

Top airline flying from Calgary to Simpson Bay

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 492AverageC$ 746FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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