$110 Cheap Flights from Portland (PWM) to Philipsburg (SXM)

View $110 flight on Mon, Mar 30, 2026Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)

Cheap Flights from Portland to Philipsburg (PWM-SXM)

Prices were available within the past 7 days and start at $110 for one-way flights and $293 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Jan 19 - Wed, Jan 28
PWM
Portland
SXM
Saint Martin
$293 Roundtrip, found 3 days ago
$293
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jan 19 from Portland to Saint Martin, returning Wed, Jan 28, priced at $293 found 3 days ago
JetBlue Airways
Mon, Mar 30 - Wed, Apr 15
PWM
Portland
SXM
Saint Martin
$295 Roundtrip, found 5 days ago
$295
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Mar 30 from Portland to Saint Martin, returning Wed, Apr 15, priced at $295 found 5 days ago
American Airlines
Thu, Jan 22 - Fri, Jan 30
PWM
Portland
SXM
Saint Martin
$300 Roundtrip, found 6 days ago
$300
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 22 from Portland to Saint Martin, returning Fri, Jan 30, priced at $300 found 6 days ago
American Airlines
Thu, Jan 22 - Fri, Jan 30
PWM
Portland
SXM
Saint Martin
$300 Roundtrip, found 6 days ago
$300
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 22 from Portland to Saint Martin, returning Fri, Jan 30, priced at $300 found 6 days ago
American Airlines
Thu, Jan 22 - Fri, Jan 30
PWM
Portland
SXM
Saint Martin
$302 Roundtrip, found 6 days ago
$302
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 22 from Portland to Saint Martin, returning Fri, Jan 30, priced at $302 found 6 days ago
American Airlines
Mon, Jan 19 - Wed, Jan 28
PWM
Portland
SXM
Saint Martin
$303 Roundtrip, found 3 days ago
$303
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jan 19 from Portland to Saint Martin, returning Wed, Jan 28, priced at $303 found 3 days ago
American Airlines
Fri, Mar 6 - Fri, Mar 13
PWM
Portland
SXM
Saint Martin
$306 Roundtrip, found 2 days ago
$306
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Mar 6 from Portland to Saint Martin, returning Fri, Mar 13, priced at $306 found 2 days ago
Delta
Mon, Feb 2 - Sun, Feb 8
PWM
Portland
SXM
Saint Martin
$307 Roundtrip, found 19 hours ago
$307
Roundtrip
found 19 hours ago
Select Delta flight, departing Mon, Feb 2 from Portland to Saint Martin, returning Sun, Feb 8, priced at $307 found 19 hours ago
United
Mon, Mar 23 - Tue, Mar 31
PWM
Portland
SXM
Saint Martin
$331 Roundtrip, found 22 hours ago
$331
Roundtrip
found 22 hours ago
Select United flight, departing Mon, Mar 23 from Portland to Saint Martin, returning Tue, Mar 31, priced at $331 found 22 hours ago
Air Canada
Thu, Mar 5 - Tue, Mar 17
PWM
Portland
SXM
Saint Martin
$1,009 Roundtrip, found 2 days ago
$1,009
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Mar 5 from Portland to Saint Martin, returning Tue, Mar 17, priced at $1,009 found 2 days ago

Alternative airports near Simpson Bay

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Princess Juliana Intl. SXM. Cheapest option available. Flights from $415
SXM
Princess Juliana Intl.
Cheapest
Flights from $415
Flights from Portland (PWM) to Philipsburg (SXM)
Origin airport
Portland Intl. Jetport
Destination airport
Princess Juliana Intl.
Airlines serving
Air Canada, American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$293
Distance
1818 mi

Portland to Philipsburg Flights

The cheapest times to fly from Portland to Philipsburg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Philipsburg are during the month of January. You can find some of the cheapest flights from Portland to Philipsburg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Philipsburg

Sunday is one of the best days to book for cheap flights from Portland to Philipsburg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Philipsburg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Philipsburg in 2026. You can also book with separate airlines for your outbound and return journeys, from $110 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Philipsburg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Philipsburg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM) cost?
Snag a cheap one-way flight from $110 or cheap return flight from $293 from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)?
January is the most affordable month to fly from PWM to SXM. Traveling during an off-peak travel window is often the key to better flight prices.
What is the cheapest airline that flies from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)?
To find the cheapest airline flying from PWM to SXM, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)?
There aren't any daily nonstop flights available from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM). But you can book flights with layovers. Filter your search on Expedia to include one or two stops, and you'll be on your way in no time.
What day of the week has the most flights from PWM to SXM?
Typically you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)?
To avoid potential delays on the Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM) route, travel before 3 PM. Later flights have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM) last-minute?
Booking your flight from PWM to SXM right before your journey is generally more expensive. But if there's some wiggle room with your travel dates and times, you could land a cheap last-minute fare.
Is it cheaper to book a PWM to SXM flight and hotel package?
Compared with arranging hotels and flights separately, booking a PWM to SXM flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place will take the stress out of planning your trip. Just secure your flights and select from our extensive range of stays, then customize your trip with other add-ons like tours, car rentals and activities.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to Princess Juliana Intl. Airport (SXM)?
If you reserved your PWM to SXM flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.