What is the cheapest airline that flies from Portland to Simpson Bay Princess Juliana?

American Airlines is the most popular carrier operating from Portland to Simpson Bay Princess Juliana

When did momondo last update prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport are updated daily.

How many operators does momondo search for flights from Portland Airport to Simpson Bay Princess Juliana Airport?

As of November 2025, there are 2 operators available to choose from for flights from Portland Airport to Simpson Bay Princess Juliana Airport.

How old do you have to be to fly from Portland Airport to Simpson Bay Princess Juliana Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$489 Cheap Flights from Portland to Simpson Bay in 2025/26

Q: What is the typical price of a round-trip flight between Portland and Simpson Bay?

Prices are currently low for flights on this route. Typical prices usually range from $816 to $993. The lowest price recently found on this route was $687.

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Find the cheapest flights from Portland to Simpson Bay

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9:45 pm - 1:53 pmPDX-SXM

13h 08m1 stop

12:45 pm - 10:39 pmSXM-PDX

12h 54m1 stop

$687Delta

Find Deal

Tue, Mar 31 - Wed, Apr 8

5:10 pm - 1:53 pmPDX-SXM

17h 43m2 stops

12:45 pm - 10:39 pmSXM-PDX

12h 54m1 stop

$692Delta

Find Deal

Tue, Mar 31 - Wed, Apr 8

11:07 pm - 1:10 pmPDX-SXM

11h 03m1 stop

2:25 pm - 11:02 pmSXM-PDX

11h 37m1 stop

$712American Airlines

Find Deal

Wed, Apr 29 - Thu, May 7

11:07 pm - 2:10 pmPDX-SXM

12h 03m1 stop

2:35 pm - 10:14 amSXM-PDX

22h 39m2 stops

$717American Airlines

Find Deal

Wed, Apr 29 - Thu, May 7

10:49 pm - 2:26 pmPDX-SXM

11h 37m1 stop

2:03 pm - 11:46 pmSXM-PDX

13h 43m1 stop

$737American Airlines

Find Deal

Fri, Jan 2 - Mon, Jan 12

3:15 pm - 1:40 pmPDX-SXM

43h 25m2 stops

12:25 pm - 9:15 amSXM-PDX

23h 50m2 stops

$1,057Multiple Airlines

Find Deal

Fri, Mar 20 - Sat, Mar 28

9:00 am - 3:57 pmPDX-SXM

26h 57m2 stops

2:52 pm - 6:41 pmSXM-PDX

31h 49m3 stops

$1,072United Airlines

Find Deal

Fri, Jan 2 - Mon, Jan 12

3:15 pm - 1:40 pmPDX-SXM

43h 25m2 stops

12:25 pm - 9:15 amSXM-PDX

23h 50m3 stops

$1,099Multiple Airlines

Find Deal

Fri, Mar 20 - Sat, Mar 28

11:10 pm - 12:50 pmPDX-SXM

10h 40m1 stop

3:55 pm - 12:00 pmSXM-PDX

23h 05m2 stops

$1,376United Airlines

Find Deal

Tue, Mar 10 - Wed, Mar 11

7:00 pm - 2:40 pmPDX-SXM

15h 40m2 stops

3:40 pm - 9:15 amSXM-PDX

45h 35m2 stops

$2,367Air Canada

Find Deal

Fri, Nov 21 - Sat, Nov 29

American Airlines flights from Portland to Simpson Bay

Our best American Airlines deals on Portland to Simpson Bay flight tickets

American Airlines

Apr 29

PDX11:07 pmPortland

11h 03m

1 stop

SXM1:10 pmSimpson Bay Princess Juliana

May 7

SXM2:25 pmSimpson Bay Princess Juliana

11h 37m

1 stop

PDX11:02 pmPortland

$712

Find similar

American Airlines

Apr 29

PDX11:07 pmPortland

12h 03m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

May 7

SXM2:35 pmSimpson Bay Princess Juliana

22h 39m

2 stops

PDX10:14 amPortland

$717

Find similar

American Airlines

Jan 2

PDX10:49 pmPortland

11h 37m

1 stop

SXM2:26 pmSimpson Bay Princess Juliana

Jan 12

SXM2:03 pmSimpson Bay Princess Juliana

13h 43m

1 stop

PDX11:46 pmPortland

$737

Find similar

Delta flights from Portland to Simpson Bay

Our best Delta deals on Portland to Simpson Bay flight tickets

Delta

Mar 31

PDX9:45 pmPortland

13h 08m

1 stop

SXM1:53 pmSimpson Bay Princess Juliana

Apr 8

SXM12:45 pmSimpson Bay Princess Juliana

12h 54m

1 stop

PDX10:39 pmPortland

$687

Find similar

Delta

Mar 31

PDX5:10 pmPortland

17h 43m

2 stops

SXM1:53 pmSimpson Bay Princess Juliana

Apr 8

SXM12:45 pmSimpson Bay Princess Juliana

12h 54m

1 stop

PDX10:39 pmPortland

$692

Find similar

Delta

Nov 21

PDX10:10 pmPortland

12h 45m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Nov 29

SXM4:30 pmSimpson Bay Princess Juliana

24h 19m

2 stops

PDX12:49 pmPortland

$2,858

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/31

9:45 pm-1:53 pm

1 stop13h 08m

Simpson Bay Princess Juliana

Wed 4/8

12:45 pm-10:39 pm

1 stop12h 54m

$687

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/31

5:10 pm-1:53 pm

2 stops17h 43m

Simpson Bay Princess Juliana

Wed 4/8

12:45 pm-10:39 pm

1 stop12h 54m

$692

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 4/29

11:07 pm-1:10 pm

1 stop11h 03m

Simpson Bay Princess Juliana

Thu 5/7

2:25 pm-11:02 pm

1 stop11h 37m

$712

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 4/29

11:07 pm-2:10 pm

1 stop12h 03m

Simpson Bay Princess Juliana

Thu 5/7

2:35 pm-10:14 am

2 stops22h 39m

$717

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 1/2

10:49 pm-2:26 pm

1 stop11h 37m

Simpson Bay Princess Juliana

Mon 1/12

2:03 pm-11:46 pm

1 stop13h 43m

$737

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 3/20

3:15 pm-1:40 pm

2 stops43h 25m

Simpson Bay Princess Juliana

Sat 3/28

12:25 pm-9:15 am

2 stops23h 50m

$1,057

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 1/2

9:00 am-3:57 pm

2 stops26h 57m

Simpson Bay Princess Juliana

Mon 1/12

2:52 pm-6:41 pm

3 stops31h 49m

$1,072

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 3/20

3:15 pm-1:40 pm

2 stops43h 25m

Simpson Bay Princess Juliana

Sat 3/28

12:25 pm-9:15 am

3 stops23h 50m

$1,099

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 3/10

11:10 pm-12:50 pm

1 stop10h 40m

Simpson Bay Princess Juliana

Wed 3/11

3:55 pm-12:00 pm

2 stops23h 05m

$1,376

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 11/21

7:00 pm-2:40 pm

2 stops15h 40m

Simpson Bay Princess Juliana

Sat 11/29

3:40 pm-9:15 am

2 stops45h 35m

$2,367

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the typical price of a round-trip flight between Portland and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Portland to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $695. If you aren’t able to travel to Simpson Bay during the month of September, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $749.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Thursday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $677. Flights from Portland to Simpson Bay on a Friday will generally be more expensive and average around $1,107. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Portland to Simpson Bay at noon for as low as $617. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the evening when prices are around $877.

When to book flights from Portland to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Portland to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Portland to Simpson Bay (PDX to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Simpson Bay

Direct flights	None

There are no direct flights from Portland to Simpson Bay. There are no popular flight routes from Portland to Simpson Bay.

Search flight deals

How far is Portland to Simpson Bay Princess Juliana by plane?
There are 3870.0 mi between Portland and Simpson Bay Princess Juliana. In terms of flight time, this usually takes a little over 9h 33m.
When did momondo last update prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport are updated daily.
How many operators does momondo search for flights from Portland Airport to Simpson Bay Princess Juliana Airport?
As of November 2025, there are 2 operators available to choose from for flights from Portland Airport to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Portland Airport to Simpson Bay Princess Juliana Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents required for your trip to Simpson Bay Princess Juliana Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Simpson Bay Princess Juliana Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Portland to Simpson Bay?
momondo data reveals that the most frequently booked airline on the route from Portland to Simpson Bay is American Airlines, representing 80% of all bookings. The subsequent popular airline is Delta at 20%.

Best airlines flying from Portland to Simpson Bay

Compare and see reviews for airlines that fly from Portland to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $604	Free Cancellation	Rating 7.2 11,038 reviews		Search American Airlines flights
Delta	PriceFrom $687	Free Cancellation	Rating 7.9 8,002 reviews		Search Delta flights

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Why use momondo?

Why should I use momondo to find a flight deal from Portland to Simpson Bay?

It is quick and easy to find Portland to Simpson Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Simpson Bay that suits you.

Can I find flights from Portland to Simpson Bay with flexible booking policies on momondo?

Flights from Portland to Simpson Bay with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Portland to Simpson Bay?

momondo helps you find the best flight between Portland and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Portland to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Portland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Simpson Bay trip

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Cheap flights from Portland to Simpson Bay from $687

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Simpson Bay departing on 3/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Portland to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

American Airlines flights from Portland to Simpson Bay

Our best American Airlines deals on Portland to Simpson Bay flight tickets

Delta flights from Portland to Simpson Bay

Our best Delta deals on Portland to Simpson Bay flight tickets

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

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Portland to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Portland and Simpson Bay?

What is the cheapest month to fly to Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest time of day to depart on your flight to Simpson Bay?

What is the cheapest airline that flies from Portland to Simpson Bay Princess Juliana?

American Airlines is the most popular carrier operating from Portland to Simpson Bay Princess Juliana

When to book flights from Portland to Simpson Bay

Cheap Portland to Simpson Bay (PDX to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland to Simpson Bay

Direct flights

How far is Portland to Simpson Bay Princess Juliana by plane?

When did momondo last update prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Portland Airport to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly from Portland Airport to Simpson Bay Princess Juliana Airport?

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular airline from Portland to Simpson Bay?

Best airlines flying from Portland to Simpson Bay

Compare and see reviews for airlines that fly from Portland to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Simpson Bay?

Can I find flights from Portland to Simpson Bay with flexible booking policies on momondo?

How can momondo help me find flights from Portland to Simpson Bay?

I’m not ready to book a flight from Portland to Simpson Bay right now. Can momondo alert me if prices change?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo