HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$114+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pittsburgh to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 28, 2026.

This Priceline deal was found by Cheapflights users on 1/25. 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.
Thu 2/199:09 pm
PIT
-
SXM
1 stop16h 06m
Spirit Airlines
Thu 2/263:20 pm
SXM
-
PIT
1 stop9h 39m
Spirit Airlines
Deal found 1/25$275
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Fri 3/206:10 am
PIT
-
SXM
1 stop6h 40m
United Airlines
Wed 3/253:55 pm
SXM
-
PIT
1 stop7h 15m
United Airlines
Deal found 1/26$293
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/267:09 pm
PIT
-
SXM
2 stops18h 10m
American Airlines
Tue 3/102:17 pm
SXM
-
PIT
2 stops18h 54m
American Airlines
Deal found 1/27$298
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/97:21 pm
PIT
-
SXM
1 stop16h 16m
American Airlines
Sat 5/162:56 pm
SXM
-
PIT
1 stop25h 58m
American Airlines
Deal found 1/27$299
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 6/1410:53 am
PIT
-
SXM
1 stop25h 52m
American Airlines
Fri 6/194:36 pm
SXM
-
PIT
2 stops18h 34m
American Airlines
Deal found 1/27$303
This American Airlines deal was found by Cheapflights users on 1/28. 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 7/110:53 am
PIT
-
SXM
1 stop25h 52m
American Airlines
Wed 7/81:45 pm
SXM
-
PIT
1 stop20h 28m
American Airlines
Deal found 1/28$305
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 2/46:15 pm
PIT
-
SXM
1 stop19h 00m
Spirit Airlines
Sat 2/73:20 pm
SXM
-
PIT
1 stop19h 20m
Spirit Airlines
Deal found 1/27$313
This FlightHub deal was found by Cheapflights users on 1/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
PIT
-
SXM
1 stop7h 16m
Spirit Airlines
Thu 5/142:11 pm
SXM
-
PIT
1 stop9h 31m
Spirit Airlines
Deal found 1/27$324
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Tue 4/710:45 am
PIT
-
SXM
1 stop26h 23m
Spirit Airlines
Fri 4/102:14 pm
SXM
-
PIT
1 stop9h 00m
Spirit Airlines
Deal found 1/26$336
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/195:19 pm
PIT
-
SXM
2 stops18h 10m
American Airlines
Thu 2/265:01 pm
SXM
-
PIT
1 stop18h 13m
American Airlines
Deal found 1/25$343
This FlightHub deal was found by Cheapflights users on 1/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
PIT
-
SXM
1 stop7h 16m
Spirit Airlines
Wed 9/22:11 pm
SXM
-
PIT
1 stop9h 31m
Spirit Airlines
Deal found 1/26$346

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Priceline)

One-way from

$114
(Priceline)

Popular in

July

Cheapest in

September

Average price

$616
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
One-way flight from Pittsburgh to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 28, 2026.
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

Fri 3/20

6:10 am-12:50 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Wed 3/25

3:55 pm-11:10 pm

1 stop7h 15m

$293

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 5/23

7:59 pm-12:33 pm

1 stop16h 34m

Simpson Bay Princess Juliana

Thu 5/28

1:35 pm-11:30 pm

1 stop9h 55m

$293

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Fri 3/20

8:10 pm-1:21 pm

2 stops17h 11m

Simpson Bay Princess Juliana

Wed 3/25

2:17 pm-9:11 am

2 stops18h 54m

$298

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sat 5/9

4:44 pm-11:37 am

2 stops18h 53m

Simpson Bay Princess Juliana

Thu 5/14

4:35 pm-1:03 pm

2 stops20h 28m

$298

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Mon 6/1

7:45 pm-1:22 pm

2 stops17h 37m

Simpson Bay Princess Juliana

Sat 6/6

2:27 pm-8:30 am

2 stops18h 03m

$298

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 2/19

9:09 pm-2:15 pm

1 stop16h 06m

$114

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 2/19

7:09 pm-2:16 pm

2 stops18h 07m

$153

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Thu 2/19

9:33 pm-2:15 pm

3 stops39h 42m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 23, 2026.

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 31 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 $285). Flying from Pittsburgh to Simpson Bay in June 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.

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 January 28, 2026.
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
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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
9,206 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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
11,198 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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
2,889 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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
8,384 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Crew

8.5

Boarding

8.1

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, United Airlines, and American Airlines can get you from Pittsburgh to Simpson Bay in just under 6h 40m. Your travel time can differ by up to 11h 30m. 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 ($266), United Airlines ($363), and JetBlue ($366) offers the cheapest pricing from Pittsburgh to Simpson Bay. Spirit Airlines is 51% 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 $285). Flying from Pittsburgh to Simpson Bay in June 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

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.

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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$433FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$363Average$599FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$366Average$539FlexibilityNo cancel feeOn-time62%
DeltaCheapest$369Average$537FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$403Average$589FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights