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Simpson Bay

$206+ Cheap flights from Pittsburgh (PIT) to Simpson Bay (SXM)

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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Simpson Bay Princess Juliana are usually found in September or October, booked 83 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Pittsburgh to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) 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 September 11, 2025.

Round-trip from

$342
(Priceline)

One-way from

$206
(JetBlue)

Popular in

February

Cheapest in

September

Average price

$446
From Pittsburgh to Simpson Bay Princess Juliana
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One-way flight from Pittsburgh to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 16% potential increase in price ($122 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 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 Pittsburgh to Simpson Bay

Cheapest flights from Pittsburgh to Simpson Bay
Explore the most affordable flight options available from Pittsburgh to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:45 amPIT - SXM
1 stop7h 15mSpirit Airlines
Sat 11/13:05 pmSXM - PIT
1 stop8h 11mSpirit Airlines
Deal found 9/10$342
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:44 pmPIT - SXM
1 stop20h 26mSpirit Airlines
Mon 11/174:28 pmSXM - PIT
2 stops21h 45mSpirit Airlines
Deal found 9/10$400
This Expedia deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:45 amPIT - SXM
1 stop7h 15mSpirit Airlines
Sat 10/183:05 pmSXM - PIT
1 stop8h 11mSpirit Airlines
Deal found 9/11$412
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:08 pmPIT - SXM
2 stops18h 49mUnited Airlines
Sat 11/14:00 pmSXM - PIT
1 stop7h 27mUnited Airlines
Deal found 9/10$427
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:11 pmPIT - SXM
1 stop16h 49mAmerican Airlines
Sat 12/65:25 pmSXM - PIT
2 stops16h 05mAmerican Airlines
Deal found 9/8$432
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:10 amPIT - SXM
1 stop7h 09mAmerican Airlines
Fri 10/32:20 pmSXM - PIT
2 stops21h 09mAmerican Airlines
Deal found 9/9$437
This Mytrip deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:51 pmPIT - SXM
3 stops24h 39mMultiple Airlines
Sat 10/183:05 pmSXM - PIT
1 stop8h 11mMultiple Airlines
Deal found 9/11$440
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:05 pmPIT - SXM
1 stop19h 10mJetBlue
Fri 10/32:46 pmSXM - PIT
1 stop9h 02mJetBlue
Deal found 9/9$463
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amPIT - SXM
1 stop9h 22mAmerican Airlines
Mon 11/173:20 pmSXM - PIT
1 stop9h 28mAmerican Airlines
Deal found 9/10$468
This Mytrip deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:26 pmPIT - SXM
2 stops35h 59mMultiple Airlines
Mon 11/174:28 pmSXM - PIT
3 stops21h 45mMultiple Airlines
Deal found 9/10$481

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh 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 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Pittsburgh to Simpson Bay that are best for you.

Fly from

Pittsburgh

Fly to

Simpson Bay

Route

Depart

Return

Price

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/25

6:45 am-2:00 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-11:16 pm

1 stop8h 11m

$342

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 11/13

5:44 pm-3:10 pm

1 stop20h 26m

Simpson Bay Princess Juliana

Mon 11/17

4:28 pm-1:13 pm

2 stops21h 45m

$400

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/11

6:45 am-2:00 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:16 pm

1 stop8h 11m

$412

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/25

8:08 pm-2:57 pm

2 stops18h 49m

Simpson Bay Princess Juliana

Sat 11/1

4:00 pm-11:27 pm

1 stop7h 27m

$427

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 11/29

8:11 pm-2:00 pm

1 stop16h 49m

Simpson Bay Princess Juliana

Sat 12/6

5:25 pm-8:30 am

2 stops16h 05m

$432

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 11/13

6:41 am-4:22 pm

2 stops8h 41m

Simpson Bay Princess Juliana

Mon 11/17

5:24 pm-12:18 pm

2 stops19h 54m

$432

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/11

4:49 pm-1:37 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Sat 10/18

4:24 pm-9:36 am

2 stops17h 12m

$432

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 9/27

6:10 am-1:19 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Fri 10/3

2:20 pm-11:29 am

2 stops21h 09m

$437

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 10/11

6:51 pm-7:30 pm

3 stops24h 39m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:16 pm

1 stop8h 11m

$440

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 11/20

6:01 am-4:18 pm

1 stop9h 17m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 14 results
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Best time to book a flight from Pittsburgh to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Pittsburgh 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 Pittsburgh to Simpson Bay

How far ahead should I book a flight from Pittsburgh to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Simpson Bay. Price data was last updated on August 29, 2025.

The price you pay for your flight from Pittsburgh to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 82 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Simpson Bay (average of $459). Flying from Pittsburgh to Simpson Bay in March is currently the most expensive (average of $652). 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 PIT to SXM?

Find hourly flight availability from Pittsburgh 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 September 11, 2025.

When flying from Pittsburgh to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 39% versus a flight in the morning.

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 September 11, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Pittsburgh 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.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh 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 Pittsburgh to Simpson Bay?

    Spirit Airlines, United Airlines, and American Airlines can get you from Pittsburgh to Simpson Bay in just under 7h 15m. Your travel time can differ by up to 11h 34m. The distance from Pittsburgh to Simpson Bay is about 1855 mi. This flight may include one or multiple stops.

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

    According to our current data, Spirit Airlines ($342), United Airlines ($412), and Delta ($417) offers the cheapest pricing from Pittsburgh to Simpson Bay. Spirit Airlines is 44% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Pittsburgh to Simpson Bay one-way?

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $206. Copa Airlines flights start at $351 while deals on Spirit Airlines start at $395 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pittsburgh 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 Pittsburgh to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Simpson Bay (average of $459). Flying from Pittsburgh to Simpson Bay in March is currently the most expensive (average of $652). 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

Traveling 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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Top 5 airlines flying from Pittsburgh to Simpson Bay

Discover the top 5 airlines that operate flights from Pittsburgh 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 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$342Average$428FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$412Average$691FlexibilityNo cancel feeOn-time69%
DeltaCheapest$417Average$599FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$469Average$649FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$510Average$697FlexibilityNo cancel feeOn-time62%

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