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Cheap flights from Portland to Simpson Bay from $668

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 11/5. 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
1 adult, Economy, 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
1:45 pm - 2:20 pm
PDX
-
SXM
20h 35m
2 stops
Southwest Logo
3:20 pm - 10:20 am
SXM
-
PDX
23h 00m
2 stops
$668Southwest
Thu, Nov 5 - Fri, Nov 20
American Airlines Logo
10:45 pm - 4:20 pm
PDX
-
SXM
13h 35m
1 stop
American Airlines Logo
3:20 pm - 11:51 pm
SXM
-
PDX
12h 31m
1 stop
$695American Airlines
Sun, Nov 1 - Sat, Nov 7
United Airlines Logo
6:59 pm - 1:50 pm
PDX
-
SXM
14h 51m
2 stops
United Airlines Logo
2:40 pm - 9:40 am
SXM
-
PDX
23h 00m
2 stops
$700United Airlines
Sun, Nov 1 - Sat, Nov 7
Delta Logo
5:54 pm - 1:53 pm
PDX
-
SXM
16h 59m
2 stops
Delta Logo
3:18 pm - 8:37 am
SXM
-
PDX
20h 19m
2 stops
$704Delta
Sat, Aug 29 - Sun, Sep 6
American Airlines Logo
10:45 pm - 4:20 pm
PDX
-
SXM
13h 35m
1 stop
American Airlines Logo
5:24 pm - 10:58 am
SXM
-
PDX
21h 34m
2 stops
$705American Airlines
Wed, Nov 4 - Fri, Nov 13
American Airlines Logo
9:47 pm - 1:51 pm
PDX
-
SXM
13h 04m
1 stop
American Airlines Logo
2:51 pm - 11:55 pm
SXM
-
PDX
12h 04m
1 stop
$759American Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
10:15 pm - 4:20 pm
PDX
-
SXM
14h 05m
2 stops
American Airlines Logo
3:20 pm - 11:10 am
SXM
-
PDX
23h 50m
2 stops
$764American Airlines
Sun, Nov 1 - Sat, Nov 7
Delta Logo
7:55 pm - 2:49 pm
PDX
-
SXM
14h 54m
2 stops
Delta Logo
4:10 pm - 12:18 pm
SXM
-
PDX
24h 08m
2 stops
$766Delta
Fri, Nov 6 - Mon, Nov 16
United Airlines Logo
7:00 am - 12:33 pm
PDX
-
SXM
26h 33m
2 stops
United Airlines Logo
3:50 pm - 12:07 pm
SXM
-
PDX
23h 17m
3 stops
$820United Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
11:15 pm - 3:44 pm
PDX
-
SXM
13h 29m
2 stops
American Airlines Logo
4:39 pm - 11:34 am
SXM
-
PDX
21h 55m
2 stops
$833American Airlines
Wed, Jul 29 - Sat, Aug 8

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United Airlines flights from Portland to Simpson Bay

Our best United Airlines deals on Portland to Simpson Bay flight tickets
United Airlines
Nov 1
PDX6:59 pmPortland
14h 51m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Nov 7
SXM2:40 pmSimpson Bay Princess Juliana
23h 00m
2 stops
PDX9:40 amPortland
$700
United Airlines
Jul 14
PDX7:00 amPortland
26h 33m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jul 21
SXM3:50 pmSimpson Bay Princess Juliana
23h 17m
3 stops
PDX12:07 pmPortland
$820
United Airlines
Jul 31
PDX11:59 pmPortland
33h 34m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Aug 7
SXM3:50 pmSimpson Bay Princess Juliana
23h 17m
3 stops
PDX12:07 pmPortland
$846

American Airlines flights from Portland to Simpson Bay

Our best American Airlines deals on Portland to Simpson Bay flight tickets
American Airlines
Nov 1
PDX10:45 pmPortland
13h 35m
1 stop
SXM4:20 pmSimpson Bay Princess Juliana
Nov 7
SXM3:20 pmSimpson Bay Princess Juliana
12h 31m
1 stop
PDX11:51 pmPortland
$695
American Airlines
Nov 4
PDX10:45 pmPortland
13h 35m
1 stop
SXM4:20 pmSimpson Bay Princess Juliana
Nov 13
SXM5:24 pmSimpson Bay Princess Juliana
21h 34m
2 stops
PDX10:58 amPortland
$705
American Airlines
Jul 14
PDX9:47 pmPortland
13h 04m
1 stop
SXM1:51 pmSimpson Bay Princess Juliana
Jul 21
SXM2:51 pmSimpson Bay Princess Juliana
12h 04m
1 stop
PDX11:55 pmPortland
$759

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 June 16, 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

Thu 11/5

1:45 pm-2:20 pm

2 stops20h 35m

Simpson Bay Princess Juliana

Fri 11/20

3:20 pm-10:20 am

2 stops23h 00m

$668

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sun 11/1

10:45 pm-4:20 pm

1 stop13h 35m

Simpson Bay Princess Juliana

Sat 11/7

3:20 pm-11:51 pm

1 stop12h 31m

$695

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sun 11/1

6:59 pm-1:50 pm

2 stops14h 51m

Simpson Bay Princess Juliana

Sat 11/7

2:40 pm-9:40 am

2 stops23h 00m

$700

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sat 8/29

5:54 pm-1:53 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Sun 9/6

3:18 pm-8:37 am

2 stops20h 19m

$704

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 11/4

10:45 pm-4:20 pm

1 stop13h 35m

Simpson Bay Princess Juliana

Fri 11/13

5:24 pm-10:58 am

2 stops21h 34m

$705
Quickest round-trip

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 7/14

9:47 pm-1:51 pm

1 stop13h 04m

Simpson Bay Princess Juliana

Tue 7/21

2:51 pm-11:55 pm

1 stop12h 04m

$759

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Sun 11/1

10:15 pm-4:20 pm

2 stops14h 05m

Simpson Bay Princess Juliana

Sat 11/7

3:20 pm-11:10 am

2 stops23h 50m

$764

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Fri 11/6

7:55 pm-2:49 pm

2 stops14h 54m

Simpson Bay Princess Juliana

Mon 11/16

4:10 pm-12:18 pm

2 stops24h 08m

$766

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Tue 7/14

7:00 am-12:33 pm

2 stops26h 33m

Simpson Bay Princess Juliana

Tue 7/21

3:50 pm-12:07 pm

3 stops23h 17m

$820

PortlandSimpson Bay

PDX - SXM

PDXSXM

Portland

Wed 7/29

11:15 pm-3:44 pm

2 stops13h 29m

Simpson Bay Princess Juliana

Sat 8/8

4:39 pm-11:34 am

2 stops21h 55m

$833

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 August is also cheap. Prices for this month can be found on momondo for an average of $0.

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

10h 54m

Direct flights

None
The fastest flight from Portland to Simpson Bay takes 10h 54m
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 10h 54m.

  • 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
11,666 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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