PDX - SXM

$687 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 3/31. 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
$687
Overall average: $1,070
American Airlines
Tue 3/31Wed 4/8
PDX - SXM • 1 stop
Cheapest one-way
Multiple Airlines
Thu 10/30
PDX - SXM • multi-stop
Top airlines
American Airlines
Cheapest • from $687 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 21% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 (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

Tue, Mar 31 - Wed, Apr 8
American Airlines Logo
10:59 pm - 3:10 pmPDX-SXM
13h 11m1 stop
American Airlines Logo
2:25 pm - 11:02 pmSXM-PDX
11h 37m1 stop
$687American Airlines
Find Deal
Tue, Mar 31 - Wed, Apr 8
American Airlines Logo
10:47 pm - 3:10 pmPDX-SXM
13h 23m2 stops
American Airlines Logo
2:35 pm - 10:09 amSXM-PDX
22h 34m2 stops
$692American Airlines
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Sat, Feb 7 - Sun, Feb 15
American Airlines Logo
10:15 pm - 1:45 pmPDX-SXM
11h 30m1 stop
American Airlines Logo
1:41 pm - 11:59 pmSXM-PDX
14h 18m1 stop
$717American Airlines
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Tue, Mar 31 - Wed, Apr 8
United Airlines Logo
5:45 am - 12:29 pmPDX-SXM
27h 44m3 stops
United Airlines Logo
3:55 pm - 2:42 pmSXM-PDX
25h 47m2 stops
$835United Airlines
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Fri, Feb 6 - Sun, Feb 15
Delta Logo
12:40 am - 2:17 pmPDX-SXM
9h 37m1 stop
Delta Logo
1:45 pm - 10:39 pmSXM-PDX
12h 54m1 stop
$849Delta
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Tue, Mar 31 - Wed, Apr 8
United Airlines Logo
12:40 pm - 12:29 pmPDX-SXM
20h 49m2 stops
United Airlines Logo
3:55 pm - 10:15 amSXM-PDX
21h 20m3 stops
$902United Airlines
Find Deal
Sat, Feb 7 - Sun, Feb 15
Air Canada Logo
9:50 am - 2:40 pmPDX-SXM
24h 50m3 stops
Air Canada Logo
3:40 pm - 2:40 pmSXM-PDX
27h 00m3 stops
$1,109Air Canada
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Fri, Jan 2 - Mon, Jan 12
Multiple Airlines Logo
9:50 am - 12:15 pmPDX-SXM
22h 25m2 stops
Multiple Airlines Logo
4:20 pm - 2:40 pmSXM-PDX
26h 20m3 stops
$1,213Multiple Airlines
Find Deal
Fri, Nov 21 - Sat, Nov 29
Air Canada Logo
3:15 pm - 2:40 pmPDX-SXM
19h 25m2 stops
Air Canada Logo
3:40 pm - 9:15 amSXM-PDX
45h 35m2 stops
$2,282Air Canada
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Fri, Nov 21 - Sat, Nov 29
Delta Logo
10:10 pm - 2:55 pmPDX-SXM
12h 45m1 stop
Delta Logo
4:30 pm - 1:18 pmSXM-PDX
24h 48m2 stops
$2,858Delta
Find Deal
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.

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 round-trip 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 $695 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $1,268 and $1,070 respectively.

Good to know

Low seasonSeptember
Cheapest flight$687
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 6% increase in price.
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 $687 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?

    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 $926 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 $853 and an overall rating of 7.2.

  • 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 7992 reviews
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

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

Information on your arrival and departure airports

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