PIT - SXM

$158 Find Cheap Flights from Pittsburgh to Simpson Bay - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pittsburgh to Simpson Bay departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$393
Typical prices: $433-$498
American Airlines
Mon 8/24Fri 8/28
PIT - SXM • 1 stop
Cheapest one-way
$158
American Airlines
Sun 11/1
PIT - SXM • 2 stops
Top airlines
Cheapest • from $393 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
Not available
There are currently no direct flights between Pittsburgh and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $370 (round-trip)
Shortest trip • 6h 28m (one-way)
Insights
Insights
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Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Pittsburgh to Simpson Bay (PIT-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pittsburgh to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Simpson Bay

Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
6:10 am - 1:22 pm
PIT
-
SXM
7h 12m
1 stop
American Airlines Logo
2:42 pm - 11:25 pm
SXM
-
PIT
8h 43m
1 stop
$393American Airlines
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
5:21 am - 3:39 pm
PIT
-
SXM
10h 18m
2 stops
American Airlines Logo
2:42 pm - 11:25 pm
SXM
-
PIT
8h 43m
1 stop
$398American Airlines
Sat, Oct 3 - Fri, Oct 9
American Airlines Logo
6:00 am - 1:53 pm
PIT
-
SXM
7h 53m
1 stop
American Airlines Logo
2:23 pm - 11:35 pm
SXM
-
PIT
9h 12m
1 stop
$429American Airlines
Sat, Oct 10 - Sat, Oct 17
Air Canada Logo
6:00 am - 5:00 pm
PIT
-
SXM
11h 00m
1 stop
Air Canada Logo
6:00 pm - 11:32 am
SXM
-
PIT
17h 32m
1 stop
$458Air Canada
Mon, Aug 10 - Sat, Aug 15
Delta Logo
5:50 am - 1:53 pm
PIT
-
SXM
8h 03m
1 stop
Delta Logo
3:18 pm - 9:08 am
SXM
-
PIT
17h 50m
1 stop
$469Delta
Sun, Aug 9 - Sat, Aug 15
American Airlines Logo
8:09 pm - 3:39 pm
PIT
-
SXM
19h 30m
2 stops
American Airlines Logo
4:39 pm - 11:33 am
SXM
-
PIT
18h 54m
2 stops
$470American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
5:26 pm - 1:23 pm
PIT
-
SXM
19h 57m
2 stops
American Airlines Logo
2:50 pm - 10:04 am
SXM
-
PIT
19h 14m
2 stops
$474American Airlines
Fri, Aug 14 - Thu, Aug 20
American Airlines Logo
7:39 pm - 12:44 pm
PIT
-
SXM
17h 05m
1 stop
American Airlines Logo
4:39 pm - 8:46 am
SXM
-
PIT
16h 07m
2 stops
$476American Airlines
Sat, Oct 10 - Sat, Oct 17
American Airlines Logo
5:26 pm - 1:23 pm
PIT
-
SXM
19h 57m
2 stops
American Airlines Logo
2:50 pm - 10:04 am
SXM
-
PIT
19h 14m
2 stops
$477American Airlines
Sun, Nov 29 - Thu, Dec 3
American Airlines Logo
6:01 am - 2:17 pm
PIT
-
SXM
7h 16m
1 stop
American Airlines Logo
3:20 pm - 11:58 pm
SXM
-
PIT
9h 38m
1 stop
$479American Airlines
Booking Insights

KAYAK's insights & trends for Pittsburgh to Simpson Bay flights

Get data-powered insights and trends into flights from Pittsburgh to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Pittsburgh to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pittsburgh to Simpson Bay departing in August.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pittsburgh to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pittsburgh to Simpson Bay is February, where tickets cost $360 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $1,123 and $634 respectively.

Good to know

Low season

December

Cheapest flight

$158
Best time to beat the crowds but there is an average 113% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Pittsburgh to Simpson Bay

When to book flights from Pittsburgh to Simpson Bay

Are your dates flexible? Find out the best times to travel from Pittsburgh to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Pittsburgh to Simpson Bay

  • What is the cheapest flight from Pittsburgh to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Pittsburgh to Simpson Bay was $158 for a one-way ticket and $393 for a round-trip.

  • Do I need a passport to fly between Pittsburgh and Simpson Bay?

    Yes, you’ll need a passport to travel to Simpson Bay from Pittsburgh.

  • Which airports will I be using when flying from Pittsburgh to Simpson Bay?

    Pittsburgh airport is called Pittsburgh and the only airport in Simpson Bay is Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Pittsburgh to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Pittsburgh to Simpson Bay?

    Star Alliance, and oneworld are the airline alliances operating flights between Pittsburgh and Simpson Bay, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Pittsburgh to Simpson Bay, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Pittsburgh to Simpson Bay are Southwest and United Airlines. With an average price for the route of $641 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $478 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Pittsburgh to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pittsburgh to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pittsburgh to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Pittsburgh is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pittsburgh to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Pittsburgh with another airline. Booking your flights between Pittsburgh and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pittsburgh to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Pittsburgh up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Pittsburgh to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Pittsburgh to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pittsburgh to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

For my birthday trip this was my second time ever flying, this trip was the best.

I really wish that SW would ask anyone with a carry-on to wait while those who don’t have to access the overhead bins are boarded. Then, reverse that when the plane arrives. Those without the need to clog up the aisle retrieving their bags from the overhead bins wait for those exiting the plane without needing to clog up. The aisle.

We boarded the flight and set two and a half hours on the jetway. Would have been better if they had not boarded us at all. Plane was hot and it was limited ability to access the restrooms or get a drink of water. Very unpleasant experience

The actual flight was great! The 3 hour delay not so much.

Southwest is a garbage airline and the people who fly it are garbage people.

Boarding was easy. Plane wasn’t crowded. Plenty of space. Flight was on time. Crew was pleasant.

It was great. All the crew were professional and nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

My husband and I recently had an unfortunate experience with Lufthansa. At the Philadelphia International airport, the ground staff refused to board us because we didn’t have a current visa stamped on our passports for Frankfurt. We completely understand that this was our mistake. we should have double-checked the visa requirements before our trip. However, the issue that upset us most was how the situation was handled by the staff. They told us they would mark it as “boarding denied due to visa issue”, but instead they recorded it as “no show”. Because of that incorrect entry, our return flight was automatically cancelled as well, which caused additional stress and expense. Mistakes can happen, but we expected more transparency and accuracy from a reputed airline like Lufthansa. It would have made a big difference if the staff had been more careful and considerate in documenting the situation correctly.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

A three (3) hour flight should have meal service in First Class, not just potato chips!

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

Seats suck. Only one drink service in three hours with the flight attendants being more attendant to their phones than the customer. Painful in the extreme.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

Not much space for someone 6 feet high in normal economy seat. My knee hurt

Getting to Scotland with no luggage (no medicine, no clothes and no club) on golf trip very disappointed

Quick flight again no one illness why there were multiple delays and changing of the gate number.

Seat comfort was poor (no lumbar or lower back support).

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

The American flight was a connecting flight to an international flight. The international flight has a 2 check bag rule. Despite being informed of this, American would only check 1 bag and wanted 100 to check the second (basically a 3rd carry-on) to NYC. Subsequently tsa took a sealed container of maple syrup and a few other things that couldn't be in carry-on plus I had to lug around 3 pieces of luggage for the entire trip. The American reservation was made with the international and American actually checked the one piece the entire way to China. This is one of the reasons that I will avoid American airlines if possible in the future.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

It was a good flight. Of course it was full, but it went well.

Baggage claim took too long and priority bags were not delivered first.

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

It was a smooth flight and the pilot was very pleasant

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

As with all airline's seats, a little more padding would appreciated. Especially on longer flights.

Everything you need to know for your flight from Pittsburgh to Simpson Bay

Information on your arrival and departure airports