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Simpson Bay

$244+ Cheap flights from Pittsburgh (PIT) to Simpson Bay (SXM)

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SXM
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
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 86 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap 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 December 14, 2025.

This Expedia deal was found by Cheapflights users on 12/12. 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.
Fri 12/1910:53 amPIT - SXM
1 stop26h 22mMultiple Airlines
Mon 12/224:25 pmSXM - PIT
1 stop7h 31mMultiple Airlines
Deal found 12/12$399
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Fri 12/1910:53 amPIT - SXM
1 stop26h 22mSpirit Airlines
Mon 12/223:20 pmSXM - PIT
2 stops32h 39mSpirit Airlines
Deal found 12/12$419
This American Airlines deal was found by Cheapflights users on 12/12. 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.
Fri 12/196:00 amPIT - SXM
1 stop9h 33mAmerican Airlines
Mon 12/222:59 pmSXM - PIT
1 stop10h 26mAmerican Airlines
Deal found 12/12$468
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/316:38 amPIT - SXM
1 stop6h 24mAmerican Airlines
Sat 1/35:05 pmSXM - PIT
2 stops17h 37mAmerican Airlines
Deal found 12/14$1,343
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amPIT - SXM
1 stop7h 50mDelta
Sat 1/35:22 pmSXM - PIT
1 stop7h 57mDelta
Deal found 12/14$1,546

Find 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 December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$244
(Expedia)

Popular in

January

Cheapest in

September

Average price

$599
Provider with most accurate pricing for Pittsburgh-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-Simpson Bay Princess Juliana flights.
Search Deals
From Pittsburgh to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 14, 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 1/17

5:50 pm-2:10 pm

1 stop19h 20m

Simpson Bay Princess Juliana

Thu 1/22

3:15 pm-11:44 pm

1 stop9h 29m

$244

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Tue 1/27

7:39 pm-4:28 pm

2 stops19h 49m

Simpson Bay Princess Juliana

Tue 2/3

3:09 pm-9:33 am

2 stops19h 24m

$290

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Wed 1/7

6:44 pm-3:22 pm

2 stops19h 38m

Simpson Bay Princess Juliana

Sat 1/10

5:33 pm-10:27 am

2 stops17h 54m

$290

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 2/26

6:52 pm-2:20 pm

2 stops18h 28m

Simpson Bay Princess Juliana

Tue 3/10

4:28 pm-7:30 am

2 stops15h 02m

$290

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 2/26

6:52 pm-2:20 pm

2 stops18h 28m

Simpson Bay Princess Juliana

Mon 3/9

4:28 pm-10:22 am

2 stops17h 54m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Compare providers for flights from Pittsburgh to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Simpson Bay in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pittsburgh-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pittsburgh-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pittsburgh-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 December 12, 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 86 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, February is the cheapest month in which you can book a flight from Pittsburgh to Simpson Bay (average of $297). Flying from Pittsburgh to Simpson Bay in April is currently the most expensive (average of $435). 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 December 14, 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 evening, which can drop the price by up to 39% versus a flight in the morning.

How much does it cost to fly round-trip from Pittsburgh 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 December 14, 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
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,094 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,895 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,185 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Overall

7.9

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 and American Airlines can get you from Pittsburgh to Simpson Bay in just under 19h 20m. Your travel time can differ by up to 29m. 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), Delta ($384), and JetBlue ($388) offers the cheapest pricing from Pittsburgh to Simpson Bay. Spirit Airlines is 43% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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, February is the cheapest month in which you can book a flight from Pittsburgh to Simpson Bay (average of $297). Flying from Pittsburgh to Simpson Bay in April is currently the most expensive (average of $435). 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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$342Average$433FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$388Average$549FlexibilityNo cancel feeOn-time62%
DeltaCheapest$417Average$593FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$427Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$471Average$649FlexibilityNo cancel feeOn-time71%

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