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Cheap flights from Portland to Simpson Bay from $418

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Simpson Bay departing on 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:00 pm - 1:45 pm
PDX
-
SXM
14h 45m
2 stops
Southwest Logo
3:00 pm - 10:45 am
SXM
-
PDX
22h 45m
2 stops
$694Southwest
Fri, Oct 16 - Fri, Oct 30
Southwest Logo
1:15 pm - 12:40 pm
PDX
-
SXM
20h 25m
2 stops
Southwest Logo
2:25 pm - 9:30 am
SXM
-
PDX
22h 05m
2 stops
$732Southwest
Sat, May 30 - Fri, Jun 5
Multiple Airlines Logo
2:20 pm - 4:17 pm
PDX
-
SXM
46h 57m
2 stops
Multiple Airlines Logo
3:20 pm - 1:50 pm
SXM
-
PDX
25h 30m
2 stops
$781Multiple Airlines
Thu, Jun 18 - Mon, Jun 22
American Airlines Logo
9:57 pm - 3:42 pm
PDX
-
SXM
14h 45m
2 stops
American Airlines Logo
2:53 pm - 11:59 pm
SXM
-
PDX
12h 06m
1 stop
$795American Airlines
Sat, May 30 - Fri, Jun 5
American Airlines Logo
9:47 pm - 1:50 pm
PDX
-
SXM
13h 03m
1 stop
American Airlines Logo
2:53 pm - 11:59 pm
SXM
-
PDX
12h 06m
1 stop
$815American Airlines
Thu, Jun 18 - Mon, Jun 22
American Airlines Logo
9:47 pm - 1:50 pm
PDX
-
SXM
13h 03m
1 stop
American Airlines Logo
2:22 pm - 10:25 am
SXM
-
PDX
23h 03m
2 stops
$820American Airlines
Thu, Jun 18 - Mon, Jun 22
Multiple Airlines Logo
11:29 pm - 10:05 am
PDX
-
SXM
31h 36m
2 stops
Multiple Airlines Logo
3:20 pm - 1:50 pm
SXM
-
PDX
25h 30m
2 stops
$822Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
American Airlines Logo
9:57 pm - 1:50 pm
PDX
-
SXM
12h 53m
1 stop
American Airlines Logo
2:53 pm - 11:59 pm
SXM
-
PDX
12h 06m
1 stop
$828American Airlines
Sat, May 30 - Fri, Jun 5
American Airlines Logo
10:44 pm - 1:00 pm
PDX
-
SXM
11h 16m
1 stop
American Airlines Logo
4:30 pm - 10:57 am
SXM
-
PDX
21h 27m
2 stops
$835American Airlines
Fri, Oct 16 - Fri, Oct 30
American Airlines Logo
11:58 pm - 3:05 pm
PDX
-
SXM
12h 07m
2 stops
American Airlines Logo
2:50 pm - 9:14 am
SXM
-
PDX
21h 24m
2 stops
$840American Airlines
Wed, Oct 14 - Tue, Oct 20

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American Airlines flights from Portland to Simpson Bay

Our best American Airlines deals on Portland to Simpson Bay flight tickets
American Airlines
May 30
PDX9:57 pmPortland
14h 45m
2 stops
SXM3:42 pmSimpson Bay Princess Juliana
Jun 5
SXM2:53 pmSimpson Bay Princess Juliana
12h 06m
1 stop
PDX11:59 pmPortland
$795
American Airlines
Jun 18
PDX9:47 pmPortland
13h 03m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
Jun 22
SXM2:53 pmSimpson Bay Princess Juliana
12h 06m
1 stop
PDX11:59 pmPortland
$815
American Airlines
Jun 18
PDX9:47 pmPortland
13h 03m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
Jun 22
SXM2:22 pmSimpson Bay Princess Juliana
23h 03m
2 stops
PDX10:25 amPortland
$820

Southwest flights from Portland to Simpson Bay

Our best Southwest deals on Portland to Simpson Bay flight tickets
Southwest
Oct 16
PDX8:00 pmPortland
14h 45m
2 stops
SXM1:45 pmSimpson Bay Princess Juliana
Oct 30
SXM3:00 pmSimpson Bay Princess Juliana
22h 45m
2 stops
PDX10:45 amPortland
$694
Southwest
May 30
PDX1:15 pmPortland
20h 25m
2 stops
SXM12:40 pmSimpson Bay Princess Juliana
Jun 5
SXM2:25 pmSimpson Bay Princess Juliana
22h 05m
2 stops
PDX9:30 amPortland
$732

momondo Fare Finder

 
Customize your flight search to find flights from Portland to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 1, 2026.
Use the filters below to find and compare flights from Portland to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 10/16

8:00 pm-1:45 pm

2 stops14h 45m

Simpson Bay Princess Juliana

Fri 10/30

3:00 pm-10:45 am

2 stops22h 45m

$694

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 5/30

1:15 pm-12:40 pm

2 stops20h 25m

Simpson Bay Princess Juliana

Fri 6/5

2:25 pm-9:30 am

2 stops22h 05m

$732

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 6/18

2:20 pm-4:17 pm

2 stops46h 57m

Simpson Bay Princess Juliana

Mon 6/22

3:20 pm-1:50 pm

2 stops25h 30m

$781

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 5/30

9:57 pm-3:42 pm

2 stops14h 45m

Simpson Bay Princess Juliana

Fri 6/5

2:53 pm-11:59 pm

1 stop12h 06m

$795

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 6/18

9:47 pm-1:50 pm

1 stop13h 03m

Simpson Bay Princess Juliana

Mon 6/22

2:53 pm-11:59 pm

1 stop12h 06m

$815

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 6/18

9:47 pm-1:50 pm

1 stop13h 03m

Simpson Bay Princess Juliana

Mon 6/22

2:22 pm-10:25 am

2 stops23h 03m

$820

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Thu 6/18

11:29 pm-10:05 am

2 stops31h 36m

Simpson Bay Princess Juliana

Sun 6/21

3:20 pm-1:50 pm

2 stops25h 30m

$822
Quickest round-trip

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 5/30

9:57 pm-1:50 pm

1 stop12h 53m

Simpson Bay Princess Juliana

Fri 6/5

2:53 pm-11:59 pm

1 stop12h 06m

$828

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 10/16

10:44 pm-1:00 pm

1 stop11h 16m

Simpson Bay Princess Juliana

Fri 10/30

4:30 pm-10:57 am

2 stops21h 27m

$835

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 10/14

11:58 pm-3:05 pm

2 stops12h 07m

Simpson Bay Princess Juliana

Tue 10/20

2:50 pm-9:14 am

2 stops21h 24m

$840

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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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?

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 $0. If you aren’t able to travel to Simpson Bay during the month of September, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $740.

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

Fastest flight time

14h 45m

Direct flights

None
The fastest flight from Portland to Simpson Bay takes 14h 45m
There are no direct flights from Portland to Simpson Bay. There are no popular flight routes from Portland to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Portland to Simpson Bay

  • 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 14h 45m.

  • 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?

  • 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?

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 AirlinesPriceFrom $712Free CancellationRating
7.1
11,684 reviews
Search American Airlines flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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.

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