$148 Find Cheap Flights from Caribbean to Oregon

1 adult
1 adult, Economy, 0 bags

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Useful Info

Good to know

Low seasonSeptember
Cheapest flight$148
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean to Oregon

  • How does KAYAK find such low prices on flights from Caribbean to Oregon?

    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 Caribbean to Oregon.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to 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 Caribbean to Oregon?

    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 from Caribbean to Oregon with an airline and back with another airline.

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

    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 from Caribbean to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Oregon?

    There are 6 airports in Oregon. The busiest airport is Portland Airport (PDX), with 74% of all flights arriving there.

  • What is the cheapest month to fly from Caribbean to Oregon?

    The cheapest month for flights from Caribbean to Oregon is September, when tickets cost $461 (return) on average. On the other hand, the most expensive months are June and January, when the average cost of round-trip tickets is $655 and $569 respectively.

  • How far in advance should I book a flight from Caribbean to Oregon?

    To get a below average price on the flight from Caribbean to Oregon, you should book around 4 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

  • How long is the flight to Oregon?

    An average nonstop flight from Caribbean to Oregon takes 19h 27m, covering a distance of 3355 miles. The shortest route is Christiansted (STX) to Boise (BOI) with an average flight time of 10h 01m.

  • What are the most popular destinations in Oregon?

    Based on KAYAK flight searches, the most popular destination is Portland (90% of total searches to Oregon). The next most popular destinations are Boise (9%) and Redmond (1%).

Reviews of the top 4 airlines serving from Caribbean to Oregon

 
Need help choosing which airline to fly with from Caribbean to Oregon? 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
SouthwestOverall score based on 4301 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

alike schedule and times it’s very good for me, I will stay wad delta for ever

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

Crew was tired as we all were. Pretty abrupt. Flight was delayed. Not as enjoyable as the other 3 legs we flew.

Flight attendants were friendly & good service, food sucks, seats uncomfortable, not many Asian movies or shows flying from Hong Kong

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Flight attendants had a little attitude. Food tastes no good.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

We were delayed and due to lateness we were traveling from 11pm we were rerouted to FLL and couldnt deplane but stayed on the plane with no extra Service given (extra good options etc$ there Were so many things that could go wrong and did. This was not an enjoyable experience at all thoroughly exhausting

Everything you need to know for your flight to Oregon

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.