$107 Find Cheap Flights from Portland to Caribbean - Compare and Save

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 Caribbean departing on 8/6. 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.
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Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$370
Santo Domingo
Santo Domingo1 stop$500
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestad1 stop$404
Nassau
Nassau1 stop$341
Kingston
Kingston2 stops$439
Simpson Bay
Simpson Bay2 stops$310
Providenciales
Providenciales1 stop$713
George Town
George Town2 stops$342
Puerto Plata
Puerto Plata1 stop$719
Punta Cana
Punta Cana1 stop$370
Santo Domingo
Santo Domingo1 stop$500
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestad1 stop$404
Nassau
Nassau1 stop$341
Kingston
Kingston2 stops$439
Simpson Bay
Simpson Bay2 stops$310
Providenciales
Providenciales1 stop$713
George Town
George Town2 stops$342
Puerto Plata
Puerto Plata1 stop$719

Book Cheap Portland to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Caribbean 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 Caribbean

Mon, Nov 23 - Thu, Dec 3
American Airlines Logo
6:39 pm - 3:15 pm
PWM
-
STT
19h 36m
2 stops
American Airlines Logo
6:17 pm - 11:37 am
STT
-
PWM
18h 20m
2 stops
$260American Airlines
Sat, Oct 17 - Wed, Oct 21
American Airlines Logo
7:24 pm - 3:39 pm
PWM
-
SXM
20h 15m
2 stops
American Airlines Logo
4:39 pm - 11:03 am
SXM
-
PWM
18h 24m
2 stops
$310American Airlines
Mon, Nov 9 - Mon, Nov 16
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m
1 stop
United Airlines Logo
2:05 am - 2:20 pm
SJU
-
PWM
13h 15m
2 stops
$318United Airlines
Sat, Sep 19 - Fri, Sep 25
United Airlines Logo
6:00 am - 2:44 pm
PWM
-
SJU
8h 44m
1 stop
United Airlines Logo
1:00 am - 9:08 am
SJU
-
PWM
8h 08m
1 stop
$322United Airlines
Sat, Sep 19 - Sat, Sep 26
JetBlue Logo
6:00 am - 4:51 pm
PWM
-
SJU
10h 51m
2 stops
JetBlue Logo
9:30 am - 11:52 pm
SJU
-
PWM
14h 22m
2 stops
$339JetBlue
Mon, Nov 9 - Tue, Nov 17
Southwest Logo
1:40 pm - 12:55 am
PWM
-
SJU
10h 15m
2 stops
Southwest Logo
5:45 am - 2:50 pm
SJU
-
PWM
10h 05m
2 stops
$347Southwest
Mon, Nov 16 - Fri, Nov 20
Delta Logo
6:00 am - 1:30 pm
PWM
-
NAS
7h 30m
1 stop
Delta Logo
2:55 pm - 10:23 pm
NAS
-
PWM
7h 28m
1 stop
$360Delta
Wed, Sep 9 - Thu, Sep 17
Delta Logo
6:02 am - 11:34 am
PWM
-
MBJ
6h 32m
1 stop
Delta Logo
12:59 pm - 11:56 pm
MBJ
-
PWM
9h 57m
1 stop
$362Delta
Wed, Oct 21 - Wed, Oct 28
Southwest Logo
12:55 pm - 11:45 pm
PWM
-
SJU
10h 50m
2 stops
Southwest Logo
12:40 pm - 10:35 pm
SJU
-
PWM
9h 55m
2 stops
$366Southwest
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
6:41 am - 3:59 pm
PWM
-
SJU
9h 18m
1 stop
JetBlue Logo
7:25 am - 1:45 pm
SJU
-
PWM
6h 20m
1 stop
$383JetBlue
Booking Insights

KAYAK's insights & trends for Portland to Caribbean flights

Get data-powered insights and trends into flights from Portland to Caribbean 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 Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Caribbean, 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 Caribbean is February, when tickets cost $101 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $308 and $298 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$107
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Portland to Nassau

FAQs - booking Caribbean flights

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

    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 Caribbean.

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

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

    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 Portland to Caribbean 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 Portland to Caribbean?

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

Reviews of the top 5 airlines serving from Portland to Caribbean

 
Need help choosing which airline to fly with from Portland to Caribbean? 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
SouthwestOverall score based on 4249 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

MSY had lots of coffee/breakfast options for morning flights. Bathrooms were clean. Lots of filling stations for water bottles. Delta flight was on time. The plane was clean. The staff was friendly and efficient.

London to Atlanta was good. Atlanta to Phoenix was not. Poor boarding as I had to check my rollerboard even though there was plenty of room in the bins. Crew seemed inexperienced. Sat just off the gate for nearly 30 minutes with no explanation from the pilot while the cabin got hot. I typically have a much better experience with Delta.

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

Crew was real good, flight was smooth and came in early.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

It's fine but Newark to Nashville was too long

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

Excellent communication from the staff. We actually arrived early. Very friendly and professional staff.

Excellent flight. On time. Great staff. Clean and crisp cabin.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Getting to Scotland with no luggage (no medicine, no clothes and no club) on golf trip very disappointed

My luggage never made it, I booked business class only to find out I’m sitting in the back. Very disappointed with the reservation

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

Finnair is a really good airline! We specifically looked for them on this trip. On time, great crew, and overall great experience.

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

We had multiple delays and a medical incident during the flight. We barely got a glass of water during the over 4 hours we were on the plane. Somehow first class got all of their service. It would be nice if all of your paying customers got the service they paid for.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

I just for my TSA. So security line is short and upgraded to one group up. I do think the ground crew should learn new way of boarding - the passengers sitting in higher number seat should board first to prevent traffic jam.

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports