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Simpson Bay

$149+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SXM
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Simpson Bay Princess Juliana are usually found in October or September, 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 julio 30, 2025.

Round-trip from

$361
(FlightHub)

Popular in

February

Cheapest in

October

Average price

$694
From Pittsburgh to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 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 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 julio 30, 2025.

This FlightHub deal was found by Cheapflights users on 7/29. 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.
sáb. 9/276:30 amPIT - SXM
1 stop7h 30mSpirit Airlines
sáb. 10/43:05 pmSXM - PIT
1 stop8h 17mSpirit Airlines
Deal found 7/29$361
This Flysmarter deal was found by Cheapflights users on 7/28. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/56:00 amPIT - SXM
1 stop7h 15mJetBlue
vie. 9/122:35 pmSXM - PIT
1 stop9h 13mJetBlue
Deal found 7/28$406
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/86:40 amPIT - SXM
1 stop7h 30mMultiple Airlines
mié. 11/128:57 pmSXM - PIT
2 stops23h 24mMultiple Airlines
Deal found 7/28$407
This American Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 11/87:02 pmPIT - SXM
2 stops17h 58mAmerican Airlines
mié. 11/123:20 pmSXM - PIT
2 stops19h 13mAmerican Airlines
Deal found 7/30$422
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/96:15 amPIT - SXM
1 stop6h 14mUnited Airlines
sáb. 8/163:55 pmSXM - PIT
1 stop7h 20mUnited Airlines
Deal found 7/28$825
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/288:25 pmPIT - SXM
1 stop17h 31mDelta
sáb. 8/23:21 pmSXM - PIT
1 stop9h 01mDelta
Deal found 7/28$973

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 julio 30, 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

sáb. 9/27

6:30 am-2:00 pm

1 stop7h 30m

Simpson Bay Princess Juliana

sáb. 10/4

3:05 pm-11:22 pm

1 stop8h 17m

$361

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

vie. 9/5

6:00 am-1:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

vie. 9/12

2:35 pm-11:48 pm

1 stop9h 13m

$406

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

mié. 8/27

6:00 am-3:09 pm

2 stops9h 09m

Simpson Bay Princess Juliana

mié. 9/3

2:20 pm-10:19 am

2 stops19h 59m

$422

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

vie. 9/5

10:35 am-2:00 pm

3 stops27h 25m

Simpson Bay Princess Juliana

vie. 9/12

12:25 pm-11:22 pm

3 stops34h 57m

$531

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

sáb. 8/9

6:15 am-12:29 pm

1 stop6h 14m

Simpson Bay Princess Juliana

sáb. 8/16

3:55 pm-11:15 pm

1 stop7h 20m

$825

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

lun. 9/15

6:30 am-2:00 pm

1 stop7h 30m

$149

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

lun. 9/15

6:18 pm-1:19 pm

2 stops19h 01m

$168

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

lun. 9/15

6:30 am-10:45 am

3 stops28h 15m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 25, 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 83 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 $655). 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 julio 30, 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.

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 julio 30, 2025.
Read reviews from past customers who have flown United Airlines, JetBlue, 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.
United Airlines
7.4
Good
8,896 reviews

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,896 reviews
United Airlines
7.4
Good
8,896 reviews

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
JetBlue
7.3
Good
2,913 reviews
United Airlines
7.4
Good
8,896 reviews

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,896 reviews

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Spirit Airlines
6.3
Okay
8,048 reviews
United Airlines
7.4
Good
8,896 reviews

Overall

7.4

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

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

    According to our current data, Spirit Airlines ($361), JetBlue ($406), and American Airlines ($422) offers the cheapest pricing from Pittsburgh to Simpson Bay. Spirit Airlines is 41% 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, 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 $655). 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

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Top 4 airlines flying from Pittsburgh to Simpson Bay

Discover the top 4 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$340Average$433FlexibilityNo cancel feeOn-time65%
DeltaCheapest$406Average$599FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$412Average$686FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$463Average$643FlexibilityNo cancel feeOn-time71%

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