PDX - SXM

$555 Find Cheap Flights from Portland to Simpson Bay

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Simpson Bay departing on 3/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Simpson Bay, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$555
Typical prices: $839-$1,041
Air Canada
Mon 3/2Mon 3/9
PDX - SXM • 2 stops
Cheapest one-way
Multiple Airlines
Wed 1/28
PDX - SXM • multi-stop
Top airlines
Air Canada
Cheapest • from $555 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Simpson Bay

Mon, Mar 2 - Mon, Mar 9
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
16h 55m
2 stops
Air Canada Logo
4:00 pm - 2:40 pm
SXM
-
PDX
25h 40m
2 stops
$555Air Canada
Mon, Mar 2 - Mon, Mar 9
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
16h 55m
2 stops
Air Canada Logo
4:00 pm - 9:15 am
SXM
-
PDX
44h 15m
2 stops
$586Air Canada
Mon, Mar 2 - Mon, Mar 9
Air Canada Logo
9:50 am - 4:00 pm
PDX
-
SXM
26h 10m
2 stops
Air Canada Logo
4:00 pm - 6:30 pm
SXM
-
PDX
29h 30m
2 stops
$587Air Canada
Sun, Feb 22 - Wed, Feb 25
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
40h 55m
2 stops
Air Canada Logo
5:00 pm - 9:15 am
SXM
-
PDX
44h 15m
2 stops
$658Air Canada
Sun, Feb 22 - Wed, Feb 25
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
40h 55m
2 stops
Air Canada Logo
5:00 pm - 6:30 pm
SXM
-
PDX
29h 30m
2 stops
$661Air Canada
Sun, Feb 22 - Wed, Feb 25
Air Canada Logo
7:05 pm - 4:00 pm
PDX
-
SXM
40h 55m
2 stops
Air Canada Logo
5:00 pm - 6:30 pm
SXM
-
PDX
29h 30m
2 stops
$674Air Canada
Tue, Mar 3 - Tue, Mar 10
Air Canada Logo
9:50 am - 4:00 pm
PDX
-
SXM
26h 10m
2 stops
Air Canada Logo
4:00 pm - 2:40 pm
SXM
-
PDX
25h 40m
2 stops
$678Air Canada
Tue, Mar 31 - Tue, Apr 7
American Airlines Logo
10:53 pm - 11:29 am
PDX
-
SXM
9h 36m
1 stop
American Airlines Logo
2:21 pm - 11:52 pm
SXM
-
PDX
12h 31m
1 stop
$715American Airlines
Tue, Mar 31 - Tue, Apr 7
American Airlines Logo
10:35 pm - 1:16 pm
PDX
-
SXM
11h 41m
1 stop
American Airlines Logo
2:21 pm - 10:20 am
SXM
-
PDX
22h 59m
2 stops
$720American Airlines
Wed, Apr 29 - Thu, May 7
United Airlines Logo
11:15 pm - 12:33 pm
PDX
-
SXM
10h 18m
1 stop
United Airlines Logo
1:35 pm - 9:38 am
SXM
-
PDX
23h 03m
2 stops
$723United Airlines
Booking Insights

KAYAK's insights & trends for Portland to Simpson Bay flights

Get data-powered insights and trends into flights from Portland to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland to Simpson Bay departing in March.

Good to know

Cheapest flight$555
Most popular time to fly and prices are also 10% lower on average.
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.

FAQs for booking flights from Portland to Simpson Bay

  • What is the cheapest flight from Portland to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Portland to Simpson Bay was $555 for a round-trip ticket.

  • Do I need a passport to fly between Portland and Simpson Bay?

    Yes

  • Which airports will I be using when flying from Portland to Simpson Bay?

    Portland and Simpson Bay are both served by 1 main airport. You will leave Portland from Portland and will be arriving at Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Portland to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Simpson Bay?

    oneworld is the only airline alliance operating flights between Portland and Simpson Bay.

  • How does KAYAK find such low prices on flights from Portland to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Portland with another airline. Booking your flights between Portland and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Portland to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Portland to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11201 reviews
8.0Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

10.0 ExcellentCindy, Jan 2026
MIA - BHM
Read more American Airlines reviews

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Everything you need to know for your flight from Portland to Simpson Bay

Information on your arrival and departure airports