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$491 Find cheap flights from Oregon 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 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
Tue 7/2
Tue 7/9

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Good to know

Low season

September

High season

March

Cheapest flight

$491
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Portland to Simpson Bay

FAQs for booking flights from Oregon to Simpson Bay

  • How does KAYAK find such low prices on flights from Oregon 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 Oregon to Simpson Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Oregon 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 Oregon 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 Oregon with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon 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 Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Oregon to Simpson Bay?

Find which airlines fly direct from Oregon to Princess Juliana, which days they fly and book direct flights.

Nonstop departures

Oregon to Simpson Bay Princess Juliana

Monday

Air France, American Airlines, Anguilla Air Services, +10 more

Air France, American Airlines, +11 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +12 more

Air France, American Airlines, +13 more

Wednesday

American Airlines, Anguilla Air Services, Arajet, +11 more

American Airlines, Anguilla Air Services, +12 more

Thursday

Air Century, Air France, American Airlines, +12 more

Air Century, Air France, +13 more

Friday

American Airlines, Anguilla Air Services, Caribbean Airlines, +11 more

American Airlines, Anguilla Air Services, +12 more

Saturday

Air Canada, Air France, American Airlines, +14 more

Air Canada, Air France, +15 more

Sunday

Air Canada, Air Century, Air France, +16 more

Air Canada, Air Century, +17 more

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Oregon

Monday

Air France, American Airlines, Anguilla Air Services, +10 more

Air France, American Airlines, +11 more

Tuesday

Air France, American Airlines, Anguilla Air Services, +12 more

Air France, American Airlines, +13 more

Wednesday

American Airlines, Anguilla Air Services, Arajet, +11 more

American Airlines, Anguilla Air Services, +12 more

Thursday

Air Century, Air France, American Airlines, +12 more

Air Century, Air France, +13 more

Friday

American Airlines, Anguilla Air Services, Caribbean Airlines, +11 more

American Airlines, Anguilla Air Services, +12 more

Saturday

Air Canada, Air France, American Airlines, +14 more

Air Canada, Air France, +15 more

Sunday

Air Canada, Air Century, Air France, +16 more

Air Canada, Air Century, +17 more

See more direct flights
See more direct flights

Top 3 airlines serving from Oregon to Simpson Bay

 
Need help choosing which airline to fly with from Oregon 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.
6.2
FrontierOverall score based on 3998 reviews
5.8Comfort
4.9Entertainment
7.0Crew
5.1Food
6.5Boarding
Airline reviews

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

2.0 MediocreTeddy, May 2024SAN - LAS
Read more about Frontier reviews

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

the hospitality was excellent to me and I will return flying with them

I am very disappointed. I booked with kiwi when I got to the airport there was no reservation I had to purchase another ticket after my card was already charged for almost double the cost I payed through kiwi eight days after I went to their office in Tortola and they refuse to give me a receipt so that I can cancel the original payment. They said “ there is no record that you used silver to travel “ I know I did not swim to Puerto Rico . If someone can help me please so that I can cancel the payment the credit card company said I need it, I have less than 14 days or I will loose my money. This is terrible and there is no local number for them.

I booked because of time of the flights. I needed to be at my destination at a specific time, and missed my appointment because of your delays.Get rid of these junk planes. The ATR planes are dated old scary planes. And maybe you could actually be on time. This airlines on time record is horrible. The communications between the gate agents and this company dont exist.. They couldn't give any answers,. When trying to find out when the flight would leave, they get no response when they asked for details on flights, they receivedconflicting information. I felt bad for the gate agents having to deal with Silver's inability to communicate simple information. This is my last choice in air travel. On time flights are everywhere, and both flights I took were delayed. It's a sad company.

The flight itself was good and the flight attendant was very good.

It was awesome until we ran into some bad weather but the pilots did an amazing job getting us to safety and landed

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

It was cancelled. And Kayak/Kiwi pocketed the money. Competence, ethics and customer service would be an idea.

There was nothing to like about this airline and everything needs improvement

Pros: "Nothing the flight was super late and there was no communication as to why or even and announcement to say it was late. I missed my flight to France lost a night in a hotel and missed an important event on my itinerary."
Cons: "My flight"
Cons: "it was too hot at the waiting gate in San Juan and the flight was delayed for about one hour and fifteen minutes. the terminal building smelled of mold."
Cons: "the arrival process in San Juan was horrible. passengers walk in the sun towards immigration and customs is way too long. Standing and waiting in line at immigration without any immigration officer took almost 25 minutes. that was horrible."

Book cheap flights from Oregon to Simpson Bay

Recent round-trip flight deals

8/15Thu
1 stopAmerican Airlines
14h 19mPDX-SXM
8/25Sun
1 stopAmerican Airlines
13h 15mSXM-PDX
$491
8/15Thu
2 stopsDelta
22h 19mPDX-SXM
8/25Sun
2 stopsDelta
20h 51mSXM-PDX
$495
8/15Thu
1 stopDelta
20h 15mPDX-SXM
8/25Sun
1 stopDelta
22h 37mSXM-PDX
$496
7/8Mon
2 stopsSpirit Airlines
35h 12mPDX-SXM
7/12Fri
2 stopsSpirit Airlines
34h 51mSXM-PDX
$502
7/1Mon
2 stopsAmerican Airlines
30h 39mPDX-SXM
7/8Mon
2 stopsAmerican Airlines
22h 45mSXM-PDX
$587
7/1Mon
3 stopsSpirit Airlines
34h 55mPDX-SXM
7/8Mon
3 stopsSpirit Airlines
31h 22mSXM-PDX
$593
6/13Thu
2 stopsFrontier
35h 38mPDX-SXM
6/22Sat
2 stopsFrontier
29h 17mSXM-PDX
$712
6/23Sun
2 stops
19h 08mPDX-SXM
6/30Sun
3 stops
34h 07mSXM-PDX
$863
6/23Sun
3 stops
20h 29mPDX-SXM
6/30Sun
3 stops
34h 07mSXM-PDX
$868
11/20Wed
2 stopsWestJet
34h 17mPDX-SXM
11/28Thu
2 stopsWestJet
22h 31mSXM-PDX
$2,920

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Flights to Simpson Bay

Destination:

Simpson Bay (SXM)St. Maarten

Cabin classes: