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

According to our current data, Delta ($471), American Airlines ($476), and Spirit Airlines ($515) offers the cheapest pricing from Pittsburgh to Simpson Bay. Delta is 24% cheaper than the average price of flights available within the next 90 days to this destination.

What is the cheapest day to fly from Pittsburgh to Simpson Bay?

Travelers seeking maximum savings on their Pittsburgh to Simpson Bay flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Pittsburgh to Simpson Bay?

When booking a flight from Pittsburgh to Simpson Bay, you may want to consider flying on American Airlines, Delta or Spirit Airlines as they are the most popular for this route.

What is the cheapest day to fly round-trip from Pittsburgh to Simpson Bay?

Saturday flights are found to be more expensive to fly from Pittsburgh to Simpson Bay. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Simpson Bay.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 23 days in advance, which can save you up to 108% on flights from Pittsburgh to Simpson Bay compared to booking the week you need them. Waiting 23 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $363. For sooner than that we have options available in the next 3 days from $1,149.

What is the cheapest month to fly from Pittsburgh to Simpson Bay?

Flights from Pittsburgh to Simpson Bay lean towards being more expensive in July. Prices are generally better when you fly from Pittsburgh to Simpson Bay in November, with the cheapest ticket starting at $325.

Most accurate provider : When it comes to deals on Pittsburgh-Simpson Bay flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Pittsburgh-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

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.

$417+ Flights from Pittsburgh to Simpson Bay

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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

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Cheapflights Tip: The best prices from Pittsburgh to Simpson Bay Princess Juliana are usually found in November or September, booked 22 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Pittsburgh to Simpson Bay

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$471 (Delta)
Popular in	July
Cheapest in	November
Average price	$567

Provider with most accurate pricing for Pittsburgh-Simpson Bay Princess Juliana flight deals.

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Provider most trusted by Cheapflights users for Pittsburgh-Simpson Bay Princess Juliana flights.

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From Pittsburgh to Simpson Bay Princess Juliana

Search Deals

Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

Search Deals

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 May 1, 2025.

Sun 6/16:00 pmPIT - SXM

2 stops20h 00mMultiple Airlines

Fri 6/63:05 pmSXM - PIT

1 stop8h 49mMultiple Airlines

Deal found 4/30

$417

Tue 6/175:35 amPIT - SXM

1 stop8h 25mDelta

Wed 6/253:25 pmSXM - PIT

1 stop9h 11mDelta

Deal found 4/30

$471

Tue 6/175:04 amPIT - SXM

2 stops10h 01mAmerican Airlines

Wed 6/252:34 pmSXM - PIT

1 stop8h 38mAmerican Airlines

Deal found 4/30

$476

Sun 6/112:31 pmPIT - SXM

3 stops25h 29mSpirit Airlines

Fri 6/63:05 pmSXM - PIT

3 stops23h 25mSpirit Airlines

Deal found 4/30

$498

Sun 6/16:00 amPIT - SXM

1 stop8h 43mUnited Airlines

Fri 6/61:35 pmSXM - PIT

1 stop10h 07mUnited Airlines

Deal found 4/30

$567

Tue 6/177:00 amPIT - SXM

1 stop6h 28mJetBlue

Sat 6/213:03 pmSXM - PIT

1 stop8h 48mJetBlue

Deal found 4/30

$697

Best flights from Pittsburgh to Simpson Bay
Discover carefully curated flight deals from Pittsburgh to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Tue 6/175:35 amPIT - SXM

1 stop8h 25mDelta

Wed 6/253:25 pmSXM - PIT

1 stop9h 11mDelta

Deal found 4/30

$471

Tue 6/175:04 amPIT - SXM

2 stops10h 01mAmerican Airlines

Wed 6/252:34 pmSXM - PIT

1 stop8h 38mAmerican Airlines

Deal found 4/30

$476

Sat 5/107:00 amPIT - SXM

1 stop7h 00mSpirit Airlines

Fri 5/163:05 pmSXM - PIT

1 stop8h 14mSpirit Airlines

Deal found 4/30

$515

Sat 6/217:00 amPIT - SXM

1 stop7h 00mMultiple Airlines

Sat 6/283:05 pmSXM - PIT

2 stops31h 42mMultiple Airlines

Deal found 4/30

$634

Wed 5/146:15 amPIT - SXM

1 stop6h 14mUnited Airlines

Wed 5/213:55 pmSXM - PIT

1 stop7h 16mUnited Airlines

Deal found 4/30

$672

Tue 6/177:00 amPIT - SXM

1 stop6h 28mJetBlue

Sat 6/213:03 pmSXM - PIT

1 stop8h 48mJetBlue

Deal found 4/30

$697

Last-minute flights from Pittsburgh to Simpson Bay
Discover last-minute flight deals from Pittsburgh to Simpson Bay. Data last updated May 1, 2025 and is based on user searches.

Tue 5/67:38 amPIT - SXM

1 stop6h 27mDelta

Sun 5/113:19 pmSXM - PIT

1 stop9h 02mDelta

Deal found 4/29

$832

Tue 5/65:50 amPIT - SXM

1 stop8h 15mDelta

Sun 5/113:19 pmSXM - PIT

1 stop9h 02mDelta

Deal found 4/30

$914

Sat 5/107:00 amPIT - SXM

1 stop7h 00mSpirit Airlines

Fri 5/163:05 pmSXM - PIT

1 stop8h 14mSpirit Airlines

Deal found 4/29

$491

Sat 5/107:40 pmPIT - SXM

2 stops17h 29mAmerican Airlines

Fri 5/162:05 pmSXM - PIT

1 stop10h 13mAmerican Airlines

Deal found 4/30

$767

Sat 5/107:00 amPIT - SXM

1 stop7h 00mSpirit Airlines

Fri 5/163:05 pmSXM - PIT

1 stop8h 14mSpirit Airlines

Deal found 4/30

$515

Wed 5/146:15 amPIT - SXM

1 stop6h 14mUnited Airlines

Wed 5/213:55 pmSXM - PIT

1 stop7h 16mUnited Airlines

Deal found 4/30

$672

Wed 5/145:54 amPIT - SXM

3 stops38h 36mMultiple Airlines

Wed 5/219:17 amSXM - PIT

3 stops26h 19mMultiple Airlines

Deal found 4/30

$906

Sun 5/186:00 amPIT - SXM

1 stop7h 09mAmerican Airlines

Fri 5/232:24 pmSXM - PIT

1 stop8h 24mAmerican Airlines

Deal found 4/30

$712

Cheapflights Fare Finder

Use the filters below to find and compare flights from Pittsburgh to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sun 6/1

6:00 pm-2:00 pm

2 stops20h 00m

Simpson Bay Princess Juliana

Fri 6/6

3:05 pm-11:54 pm

1 stop8h 49m

$417

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Tue 6/17

5:35 am-2:00 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Wed 6/25

3:25 pm-12:36 am

1 stop9h 11m

$471

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Tue 6/17

5:04 am-3:05 pm

2 stops10h 01m

Simpson Bay Princess Juliana

Wed 6/25

2:34 pm-11:12 pm

1 stop8h 38m

$476

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sun 6/1

12:31 pm-2:00 pm

3 stops25h 29m

Simpson Bay Princess Juliana

Fri 6/6

3:05 pm-2:30 pm

3 stops23h 25m

$498

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Sun 6/1

6:00 am-2:43 pm

1 stop8h 43m

Simpson Bay Princess Juliana

Fri 6/6

1:35 pm-11:42 pm

1 stop10h 07m

$567

PittsburghSimpson Bay

PIT - SXM

PITSXM

Pittsburgh

Tue 6/17

7:00 am-1:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Sat 6/21

3:03 pm-11:51 pm

1 stop8h 48m

$697

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Compare providers for flights from Pittsburgh to Simpson Bay

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 May.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy3 stars	Trust 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Pittsburgh-Simpson Bay flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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?

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 22 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 July is currently the most expensive (average of $669). 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?

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

To help decide which airline to fly from Pittsburgh to Simpson Bay, see what other customers have to say about Delta, United Airlines and JetBlue. 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

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,934 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,696 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

JetBlue

7.3

Good

2,922 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Spirit Airlines

6.3

Okay

7,963 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What are the cheapest airlines flying from Pittsburgh to Simpson Bay round-trip?
According to our current data, Delta ($471), American Airlines ($476), and Spirit Airlines ($515) offers the cheapest pricing from Pittsburgh to Simpson Bay. Delta is 24% 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 July is currently the most expensive (average of $669). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Pittsburgh to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$340	Average$452	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$344	Average$634	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$406	Average$640	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$412	Average$686	FlexibilityNo cancel fee	On-time69%

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$417+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Pittsburgh to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Pittsburgh to Simpson Bay Princess Juliana are usually found in November or September, booked 22 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from Pittsburgh to Simpson Bay

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Pittsburgh to Simpson Bay

Cheapest flights from Pittsburgh to Simpson BayExplore 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 May 1, 2025.

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 May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Pittsburgh to Simpson Bay that are best for you.

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 May.

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.

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 April 25, 2025.

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

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 May 1, 2025.

Reviews of airlines servicing Simpson Bay

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?

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

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

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

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

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.

Alternative routes for Pittsburgh to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Pittsburgh to Simpson Bay

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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 May 1, 2025.