Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

PDX - SXM

$494 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 8/15. 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
0 bags
Wed 6/19
Wed 6/26

Search 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
In the last 7 days travelers have searched 42,596,105 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Portland to Simpson Bay (PDX-SXM)

 
These are the cheapest deals for flights from Portland to Simpson Bay currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Portland to Simpson Bay

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Simpson Bay.

Recent one-way flight deals from Portland to Simpson Bay

Only flying one-way? Below are some of the best one-way flight deals from Portland to Simpson Bay found on KAYAK recently.

Recent last minute flight deals from Portland to Simpson Bay

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Portland to Simpson Bay.

Recent direct flight deals from Portland to Simpson Bay

The latest deals for direct flights from Portland to Simpson Bay so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Portland to Simpson Bay

Find recent round-trip train or bus tickets from Portland to Simpson Bay.

All round-trip flight deals to Simpson Bay

The cheapest plane tickets to Simpson Bay found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:05 pm - 1:19 pmPDX-SXM
12h 14m1 stop
2:15 pm - 10:28 amSXM-PDX
23h 13m2 stops
$494American Airlines
Find Deal
Thu, Aug 15 - Sun, Aug 25
2:07 pm - 1:49 pmPDX-SXM
20h 42m1 stop
3:19 pm - 10:35 amSXM-PDX
22h 16m1 stop
$496Delta
Find Deal
Thu, Aug 15 - Sun, Aug 25
12:32 am - 3:10 pmPDX-SXM
35h 38m2 stops
4:20 pm - 5:21 pmSXM-PDX
28h 01m2 stops
$597Frontier
Find Deal
Thu, Jun 13 - Sat, Jun 22
7:45 am - 3:10 pmPDX-SXM
28h 25m2 stops
4:20 pm - 5:21 pmSXM-PDX
28h 01m2 stops
$628Frontier
Find Deal
Fri, Jun 14 - Sat, Jun 22
2:00 pm - 1:48 pmPDX-SXM
20h 48m2 stops
2:44 pm - 10:56 pmSXM-PDX
35h 12m3 stops
Fri, Jun 14 - Sat, Jun 22
12:20 am - 4:49 pmPDX-SXM
13h 29m1 stop
1:30 pm - 9:38 amSXM-PDX
23h 08m1 stop
$655United Airlines
Find Deal
Fri, Jul 12 - Sat, Jul 20
12:20 am - 12:35 pmPDX-SXM
33h 15m2 stops
1:30 pm - 9:38 amSXM-PDX
23h 08m1 stop
$678United Airlines
Find Deal
Fri, Jul 12 - Sat, Jul 20
6:00 am - 1:48 pmPDX-SXM
28h 48m3 stops
2:44 pm - 10:56 pmSXM-PDX
35h 12m3 stops
Fri, Jun 14 - Sat, Jun 22
2:00 pm - 1:48 pmPDX-SXM
20h 48m2 stops
2:44 pm - 2:39 pmSXM-PDX
26h 55m2 stops
$714Spirit Airlines
Find Deal
Fri, Jun 14 - Sat, Jun 22
9:30 pm - 1:20 pmPDX-SXM
12h 50m1 stop
4:15 pm - 12:45 amSXM-PDX
11h 30m1 stop
$947American Airlines
Find Deal
Mon, Jul 8 - Sat, Jul 13

Flights from Portland to Simpson Bay - Travel Insights & Trends

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.

What is the cheapest month to fly from Portland to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Portland to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Portland to Simpson Bay is September, where tickets cost $545 on average. On the other hand, the most expensive months are August and June, where the average cost of tickets is $1,455 and $1,116 respectively.

How far in advance should I book a flight from Portland to Simpson Bay?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Portland to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Portland to Simpson Bay, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 69 days before departure.

Good to know

Low season

October

High season

January

Cheapest flight

$494
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 22% 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 $494 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, SkyTeam, and Star Alliance 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Simpson Bay are Delta and United Airlines. With an average price for the route of $676 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $906 and an overall rating of 7.4.

  • 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.

See more FAQs

Top 4 airlines serving 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.
8.0
Alaska AirlinesOverall score based on 9163 reviews
7.9Comfort
8.6Crew
7.3Food
7.3Entertainment
8.2Boarding
Airline reviews

I didn’t like not knowing my seat till I got to the airport - and my boarding group was F (last).

6.0 Goodshannon, May 2024PDX - SFO
Read more about Alaska Airlines reviews

I didn’t like not knowing my seat till I got to the airport - and my boarding group was F (last).

My boarding pass birthdate was printed incorrectly causing me to spend an extra hour in a check-in and then again TSA line and to miss a chance to have dinner pre-flight. My window seat was given away and was replaced with a middle seat. I would have liked an opportunity to charge my phone and take advantage of movies but many of the departure gate chargers weren’t operational and I don’t know of an in-flight charging option, The flight left 45 late after trouble with unruly passengers, and I was glad staff removed them.

Horrible. I likely will have to spend several thousand dollars to rebook my international flights, due to their delays, plus a hotel in SF. I can’t wait to never fly them again!

Quick easy boarding. Airport was unprepared for early landing and we were waiting in the plane for 20 minutes before getting a gate.

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

We had an hour delay Probably couldn’t be haloed Very friendly staff

dont re-route to San Jose. Re-route to closer airport. Provide shuttle bus to go to SFO, not just LYFT vouchers.

Staff seemed genuinely nice, not just going through the motions.

I would have rated the entire experience much better were it not for two things: 1. There was inconsistency between what we were told once on the plane vs. the answer I received to the question about "spreading out" from our assigned seats because the flight was sparsely populated, and the entire row we were in was empty but for us. I asked about one of us moving over one seat to make more room for us; before getting on the plane, I was told we could, which seemed like a sensible answer. Once on the plane, it was announced that we needed to stay in our assigned seats despite all of the empty space in our row, which seemed unneccessarily restrictive. 2. To add to the discomfort, we sat on the tarmac once the plane landed in Burbank for over half an hour waiting for a gate to become available. During that time we had to remain seated and buckled in, which was becoming more difficult as time dragged on, especially for my wife. If all of this was due to regulations, that may mitigate the sense of "needless" restriction somewhat, but it points to a need to make regulations less restrictive where it is not appropriate for the current conditions. The crew was not "nasty" about the restrictions, so I do not resent their actions, but it certainly would have been a much more pleasant flight if we had a few more options when it comes to comfort.

The seat side plug ins didn’t work in my row, and I ran out of things to do since my iPad and iPhone ran out of juice. The flight attendant offered me a free drink but I don’t drink. I suggested a free snack box instead and she just shrugged and walked off. Why do us non-drinkers get the short end of the stick?

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

First flight of the day… MINIMUM FUEL! 15 minute landing delay at HOU due to fog turned into a 2+ hour delay! Rather than circle, they had to divert to another city to refuel! Sat on tarmac at Austin to refuel. We ALL missed our connections! The crew, including pilots, were clueless. Crew was really a mess. At HOU, Untied employees were exceedingly rude to all. It was pitiful.

Food wasn’t very good, old business seating configuration on an old A340

An hour and a half late is UNACCEPTABLE. The negative impact to our family is unconscionable. And for the price we were forced to pay...

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Not a fan of the diagonal partially enclosed business class seats or how they have to be converted to beds manually by crew. I prefer more isolation and user control for switching to lie flat.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

The preferred seats where awful. Impossible to use them again

The flight was short. However, my bag was delayed and was put on another flight.

Flight attendant was incredible. Very efficient, friendly and pleasant. Patricia was one of the best I have ever seen. Please give her a big raise!

Delayed multiple times. Boarding was ok but getting off the aircraft was a mess. So disorganized with staff trying to help the elderly but completely blocking path for anyone else to move. Bathroom was disgusting, probably caused by one of the customers but staff couldn't care less to help clean it. No one wanted to use it since the floor was completely soaked so everyone just lined up the other restroom while the staff just chit chat with each other while looking at us.

LIT to DFW - 3 hours late; the entire plane had been boarded before they told us there was a delay due to a weather-related ground stop in Dallas. DFW to MAY - 2+ hours late due to A/C needing to be repaired after everyone had boarded, then when we finally reach the runway, the First Officer timed out and we had to taxi all the way back to the gate and wait for a new one. I arrived in New Orleans 5+ hours later than I should have. Return flights were completely cancelled; rebooked through the app to fly through CLT instead of DFW. MSY to CLT had no issues, but CLT to LIT was delayed 1.25 hrs because flight attendants had not arrived to the airport yet. At least they didn’t make us all sit on the plane to wait for them. I should have driven.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in flight WiFi Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay (especially this much) for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a terrible attitude for no reason, nor will they act the way this woman did. Unacceptable.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

Portland - Simpson Bay Flights

Departure:

Portland (undefined)United States

Destination:

Simpson Bay (SXM)St. Maarten

Cabin classes: