PWM - SXM

$160 Find Cheap Flights from Portland to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Simpson Bay departing on 6/3. 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
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Everything you should know

Cheapest round-trip
$390
American Airlines
Tue 4/28Tue 5/5
PWM - SXM • 2 stops
Cheapest one-way
$160
American Airlines
Wed 6/3
PWM - SXM • 1 stop
Top airlines
Cheapest • from $390 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $540 (round-trip)
Shortest trip • 6h 45m (one-way)
Insights
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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
Booking Insights
Flight Deals

Cheap Flights from Portland to Simpson Bay (PWM-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

Tue, Apr 28 - Tue, May 5
American Airlines Logo
7:23 pm - 1:21 pm
PWM
-
SXM
17h 58m
2 stops
American Airlines Logo
2:24 pm - 10:23 am
SXM
-
PWM
19h 59m
2 stops
$390American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
6:01 pm - 1:21 pm
PWM
-
SXM
19h 20m
2 stops
American Airlines Logo
2:21 pm - 10:18 am
SXM
-
PWM
19h 57m
2 stops
$397American Airlines
Fri, May 8 - Fri, May 15
United Airlines Logo
7:10 pm - 12:33 pm
PWM
-
SXM
17h 23m
1 stop
United Airlines Logo
1:35 pm - 11:23 pm
SXM
-
PWM
9h 48m
1 stop
$398United Airlines
Fri, May 8 - Fri, May 15
United Airlines Logo
7:10 pm - 2:43 pm
PWM
-
SXM
19h 33m
2 stops
United Airlines Logo
1:35 pm - 11:23 pm
SXM
-
PWM
9h 48m
1 stop
$403United Airlines
Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
6:54 pm - 3:42 pm
PWM
-
SXM
20h 48m
2 stops
American Airlines Logo
4:43 pm - 2:24 pm
SXM
-
PWM
21h 41m
2 stops
$414American Airlines
Wed, Jun 3 - Sun, Jun 7
United Airlines Logo
5:15 am - 12:33 pm
PWM
-
SXM
7h 18m
1 stop
United Airlines Logo
3:50 pm - 11:51 pm
SXM
-
PWM
8h 01m
1 stop
$419United Airlines
Sun, May 3 - Fri, May 8
JetBlue Logo
6:00 am - 12:34 pm
PWM
-
SXM
6h 34m
1 stop
JetBlue Logo
2:50 pm - 11:36 pm
SXM
-
PWM
8h 46m
1 stop
$447JetBlue
Wed, Jun 3 - Sun, Jun 7
United Airlines Logo
5:15 am - 12:33 pm
PWM
-
SXM
7h 18m
1 stop
United Airlines Logo
3:50 pm - 11:51 pm
SXM
-
PWM
8h 01m
1 stop
$455United Airlines
Tue, Mar 31 - Fri, Apr 10
JetBlue Logo
6:00 am - 1:28 pm
PWM
-
SXM
7h 28m
1 stop
JetBlue Logo
3:02 pm - 11:58 pm
SXM
-
PWM
8h 56m
1 stop
$477JetBlue
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
5:40 pm - 1:16 pm
PWM
-
SXM
19h 36m
2 stops
American Airlines Logo
4:35 pm - 11:15 am
SXM
-
PWM
18h 40m
2 stops
$478American 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.

Which airlines provide the cheapest flights from Portland to Simpson Bay?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Simpson Bay were found on American Airlines ($390) and United Airlines ($398).

Good to know

Low seasonSeptember
Cheapest flight$160
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 18% 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 $160 for a one-way ticket and $390 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Portland and on arrival in Simpson Bay.

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

    When flying out of Portland you will be using Portland. You will be landing at Simpson Bay, also known as 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?

    SkyTeam, and oneworld are the airline alliances operating flights between Portland and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Portland to Simpson Bay, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Simpson Bay are Delta and American Airlines. With an average price for the route of $595 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $624 and an overall rating of 7.1.

  • 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 airlines 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.
7.9
DeltaOverall score based on 8286 reviews
7.2Food
8.1Boarding
7.8Entertainment
7.9Comfort
8.5Crew
Airline reviews

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

2.0 MediocreAnonymous, Mar 2026
LAX - BNA
Read more Delta reviews

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

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

Information on your arrival and departure airports