Which airports can I use when flying from Portland to Simpson Bay?

Flights from Portland to Simpson Bay usually depart from Portland (PWM) and arrive at Simpson Bay Princess Juliana (SXM).

What cabin classes can I book on flights from Portland to Simpson Bay?

Only Economy Class is available on flights from Portland to Simpson Bay.

Which airports do connecting flights from Portland to Simpson Bay pass through?

One-stop flights from Portland to Simpson Bay most commonly connect through: • Philadelphia (PHL) - 30% of one-stop connections • New York John F Kennedy Intl (JFK) - 26% of one-stop connections • Newark (EWR) - 13% of one-stop connections • Washington, D.C. Dulles Intl (IAD) - 11% of one-stop connections Philadelphia (PHL) handles the largest share of one-stop connections on this route.

Can I save money by using flexible dates for flights from Portland to Simpson Bay?

Yes. Being flexible with your travel dates can save you up to 54% on the Portland to Simpson Bay route. Monday is the cheapest departure day at $305 round-trip on average, while Sunday is the most expensive at $658, a difference of $353. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

How long is a flight from Portland to Simpson Bay?

A nonstop flight from Portland to Simpson Bay takes 0h 00m, covering 1,817 miles.

Do I need a passport to fly from Portland to Simpson Bay?

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Have flight prices from Portland to Simpson Bay changed much recently?

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $407 to $3,232. That means the highest observed fare was about 8x higher than the lowest one.

How are flight prices from Portland to Simpson Bay looking right now?

One-way fares from Portland to Simpson Bay are currently higher than usual. Average one-way flight prices are about $529, which is 67% above the typical average for this route.

How much time can I save by choosing a different layover airport from Portland to Simpson Bay?

Flying via Philadelphia (PHL) gives the shortest average 1-stop total travel time at 7h 18m, compared with 7h 39m via Washington, D.C. Dulles Intl (IAD) and 7h 58m via Charlotte Douglas (CLT).

What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include: • Ace • Right Cars • Europcar • Budget • Alamo

How much should I expect to pay for a Portland to Simpson Bay flight?

Round-trip flights from Portland to Simpson Bay range from $561 to $652, with an average of $600 over the past 12 months. Anything below $561 counts as a good deal.

What is the cheapest airline to fly from Portland to Simpson Bay?

United Airlines ($407) and American Airlines ($436) are the cheapest airlines to fly round-trip from Portland to Simpson Bay according to KAYAK data over the last 5 days.

What is the most popular layover airport when flying from Portland to Simpson Bay?

Philadelphia (PHL) is the most popular layover for the Portland to Simpson Bay route. 30% of KAYAK users who booked 1-stop round-trips over the past 3 months connected via PHL.

What is the cheapest layover airport when flying from Portland to Simpson Bay?

Flights via Newark (EWR) offer the most affordable fares, with an average round-trip price of $519. Based on KAYAK data over the past 3 months.

When flying from Portland to Simpson Bay which airport offers the shortest layover?

Philadelphia (PHL) had the shortest average connection time for Portland to Simpson Bay layovers at 248 minutes over the past 3 months.

$292 CHEAP FLIGHTS from Portland to Simpson Bay (PWM - SXM)

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Cheapest round-trip

$407

Typical prices: $561-$652

United Airlines

Fri 2/23Fri 3/9

PWM - SXM • 1 stop

Cheapest one-way

$298

Typical prices: $316-$328

United Airlines

Tue 2/13

PWM - SXM • 2 stops

Nonstop flights

Not available

There are currently no direct flights between Portland and Simpson Bay. You'll need to take a connecting flight to reach the destination.

Insights

When to travel

November

Cheapest • 23% price drop

March

Most popular

Good to know

Top layover airports

Newark (EWR)

Cheapest • Avg $519 (round-trip)

Philadelphia (PHL)

Shortest trip • 7h 18m (one-way)

Insights

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Simpson Bay!

Flight Deals

Cheap Flights from Portland to Simpson Bay (PWM-SXM)

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Portland to Simpson Bay

Tue, Feb 23 - Tue, Mar 9

6:00 am - 1:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

6h 50m1 stop Newark

4:55 pm - 8:19 amSXM Simpson Bay Princess Juliana-PWM Portland

16h 24m2 stops Washington, D.C. Dulles Intl Newark

$407United Airlines

Tue, Feb 23 - Tue, Mar 9

6:00 am - 1:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

6h 50m1 stop Newark

4:55 pm - 8:19 amSXM Simpson Bay Princess Juliana-PWM Portland

16h 24m2 stops Washington, D.C. Dulles Intl Newark

$407United Airlines

Mon, Nov 30 - Wed, Dec 9

5:35 am - 1:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 15m1 stop Newark

2:52 pm - 11:24 pmSXM Simpson Bay Princess Juliana-PWM Portland

9h 32m1 stop Newark

$411United Airlines

Tue, Feb 23 - Tue, Mar 9

5:07 pm - 4:33 pmPWM Portland-SXM Simpson Bay Princess Juliana

22h 26m2 stops Washington, D.C. Reagan-National Miami

5:28 pm - 4:37 pmSXM Simpson Bay Princess Juliana-PWM Portland

24h 09m2 stops Miami Washington, D.C. Reagan-National

$436American Airlines

Sat, Jan 30 - Sun, Feb 7

4:00 pm - 2:29 pmPWM Portland-SXM Simpson Bay Princess Juliana

21h 29m2 stops Washington, D.C. Reagan-National Miami

1:01 pm - 9:50 amSXM Simpson Bay Princess Juliana-PWM Portland

21h 49m2 stops Miami Washington, D.C. Reagan-National

$441American Airlines

Tue, Feb 23 - Tue, Mar 9

6:00 am - 1:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

6h 50m1 stop Newark

2:52 pm - 10:57 pmSXM Simpson Bay Princess Juliana-PWM Portland

9h 05m1 stop Newark

$443United Airlines

Sat, Jan 30 - Sun, Feb 7

10:59 am - 1:52 pmPWM Portland-SXM Simpson Bay Princess Juliana

25h 53m1 stop Philadelphia

3:29 pm - 10:16 amSXM Simpson Bay Princess Juliana-PWM Portland

19h 47m2 stops Miami Philadelphia

$447American Airlines

Mon, Feb 15 - Tue, Mar 2

12:50 pm - 2:40 pmPWM Portland-SXM Simpson Bay Princess Juliana

24h 50m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

4:05 pm - 11:49 pmSXM Simpson Bay Princess Juliana-PWM Portland

8h 44m1 stop New York John F Kennedy Intl

$520Delta

Sat, Jan 30 - Sat, Feb 6

2:35 pm - 2:40 pmPWM Portland-SXM Simpson Bay Princess Juliana

23h 05m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

5:25 pm - 11:53 amSXM Simpson Bay Princess Juliana-PWM Portland

19h 28m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

$520Delta

Sun, Jan 10 - Fri, Jan 15

2:35 pm - 2:40 pmPWM Portland-SXM Simpson Bay Princess Juliana

23h 05m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

4:05 pm - 11:49 pmSXM Simpson Bay Princess Juliana-PWM Portland

8h 44m1 stop New York John F Kennedy Intl

$527Delta

Booking Insights

Price, demand and travel trends for Portland to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Portland to Simpson Bay with more confidence.

Prices

Airlines

Layovers

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

Round-trip flights from Portland to Simpson Bay start at $407. Prices are below average for this route right now, with typical round-trip fares ranging from $561 to $652. The lowest price found in the past 5 days was $407 on United Airlines.

What's the cheapest day of the week to fly from Portland to Simpson Bay?

Monday is the cheapest day of the week to fly from Portland to Simpson Bay, it is 50% cheaper than the average day. Sunday is the most expensive day with flight prices 9% higher than average. Based on deals found by KAYAK users in the last 12 months.

Find deals

Low season	August
High season	March
Cheapest flight	$298

Most popular time to fly with an average 8% increase in price.

Flight from Portland to Simpson Bay

When to book flights from Portland to Simpson Bay

Are your dates flexible? Find out the best times to travel from Portland 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.

Which airports can I use when flying from Portland to Simpson Bay?
Flights from Portland to Simpson Bay usually depart from Portland (PWM) and arrive at Simpson Bay Princess Juliana (SXM).
What cabin classes can I book on flights from Portland to Simpson Bay?
Only Economy Class is available on flights from Portland to Simpson Bay.
Which airports do connecting flights from Portland to Simpson Bay pass through?
One-stop flights from Portland to Simpson Bay most commonly connect through:

• Philadelphia (PHL) - 30% of one-stop connections
• New York John F Kennedy Intl (JFK) - 26% of one-stop connections
• Newark (EWR) - 13% of one-stop connections
• Washington, D.C. Dulles Intl (IAD) - 11% of one-stop connections

Philadelphia (PHL) handles the largest share of one-stop connections on this route.
Can I save money by using flexible dates for flights from Portland to Simpson Bay?
Yes. Being flexible with your travel dates can save you up to 54% on the Portland to Simpson Bay route. Monday is the cheapest departure day at $305 round-trip on average, while Sunday is the most expensive at $658, a difference of $353. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.
How long is a flight from Portland to Simpson Bay?
A nonstop flight from Portland to Simpson Bay takes 0h 00m, covering 1,817 miles.
Do I need a passport to fly from Portland to Simpson Bay?
Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.
Have flight prices from Portland to Simpson Bay changed much recently?
Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $407 to $3,232. That means the highest observed fare was about 8x higher than the lowest one.
How are flight prices from Portland to Simpson Bay looking right now?
One-way fares from Portland to Simpson Bay are currently higher than usual. Average one-way flight prices are about $529, which is 67% above the typical average for this route.
How much time can I save by choosing a different layover airport from Portland to Simpson Bay?
Flying via Philadelphia (PHL) gives the shortest average 1-stop total travel time at 7h 18m, compared with 7h 39m via Washington, D.C. Dulles Intl (IAD) and 7h 58m via Charlotte Douglas (CLT).
What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?
Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates starting from around $2 for economy cars. Top options include:
• Ace
• Right Cars
• Europcar
• Budget
• Alamo
How much should I expect to pay for a Portland to Simpson Bay flight?
Round-trip flights from Portland to Simpson Bay range from $561 to $652, with an average of $600 over the past 12 months. Anything below $561 counts as a good deal.

If your dates can be flexible, aim for a Monday departure instead of Sunday. On this route, Monday flights average $305 - about $353 less than Sunday (54% savings) based on the last 12 months.
If you can choose when to travel, plan your Portland to Simpson Bay trip for November. Fares historically average $459 round-trip in that month - typically $363 less than the most expensive month, which is April (based on the last 12 months).
If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.
- Hilton Vacation Club Flamingo Beach St. Maarten
- Simpson Bay Resort Marina & Spa
- The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

More options for your flight from Portland to Simpson Bay

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Other destinations

Complete your trip to Simpson Bay with a hotel stay or car rental

Car rentals in Simpson Bay

Hotels in Simpson Bay

Vacations in Simpson Bay

PWM - SXM

$292 Find Cheap Flights from Portland to Simpson Bay - Compare and Save

Everything you should know

Cheap Flights from Portland to Simpson Bay (PWM-SXM)

Recent round-trip flight deals from Portland to Simpson Bay

Recent one-way flight deals from Portland to Simpson Bay

Recent last minute flight deals from Portland to Simpson Bay

Price, demand and travel trends for Portland to Simpson Bay flights

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

What's the cheapest day of the week to fly from Portland to Simpson Bay?

What is the cheapest airline to fly from Portland to Simpson Bay?

What is the most popular layover airport when flying from Portland to Simpson Bay?

What is the cheapest layover airport when flying from Portland to Simpson Bay?

When flying from Portland to Simpson Bay which airport offers the shortest layover?

Key details for Portland to Simpson Bay flights

Low season

High season

Cheapest flight

When to book flights from Portland to Simpson Bay

Your Portland to Simpson Bay flight questions, answered

Your guide to booking Portland to Simpson Bay flights

More options for your flight from Portland to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights from Portland to Simpson Bay

Find direct flights to and from Portland and Simpson Bay

Flights to other popular destinations