$172 Find Cheap Flights from Portland to Jamaica

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 Jamaica departing on 9/1. 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

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Cheap Flights from Portland to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$728
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$728

Book Cheap Portland to Jamaica 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 Jamaica 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 Jamaica

Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
11:20 pm - 1:17 pm
PDX
-
MBJ
11h 57m
1 stop
American Airlines Logo
12:47 pm - 11:07 pm
MBJ
-
PDX
12h 20m
1 stop
$392American Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
11:20 pm - 1:34 pm
PDX
-
MBJ
12h 14m
2 stops
American Airlines Logo
12:47 pm - 11:07 pm
MBJ
-
PDX
12h 20m
1 stop
$397American Airlines
Mon, Nov 2 - Tue, Nov 10
Delta Logo
3:50 pm - 12:25 pm
PDX
-
MBJ
17h 35m
2 stops
Delta Logo
6:00 pm - 9:31 am
MBJ
-
PDX
18h 31m
2 stops
$427Delta
Sat, Jul 4 - Sat, Jul 11
United Airlines Logo
11:30 pm - 3:10 pm
PDX
-
MBJ
13h 40m
1 stop
United Airlines Logo
12:52 pm - 9:15 pm
MBJ
-
PDX
10h 23m
1 stop
$453United Airlines
Mon, Oct 19 - Tue, Oct 27
United Airlines Logo
6:45 pm - 11:43 am
PDX
-
MBJ
14h 58m
2 stops
United Airlines Logo
1:48 pm - 9:40 am
MBJ
-
PDX
21h 52m
2 stops
$458United Airlines
Tue, Aug 11 - Wed, Aug 19
Air Canada Logo
10:10 am - 1:55 pm
PDX
-
KIN
25h 45m
2 stops
Air Canada Logo
3:05 pm - 7:11 pm
KIN
-
PDX
30h 06m
2 stops
$728Air Canada
Tue, Aug 11 - Wed, Aug 19
Multiple Airlines Logo
10:10 am - 1:55 pm
PDX
-
KIN
25h 45m
2 stops
Multiple Airlines Logo
6:25 pm - 1:50 pm
KIN
-
PDX
21h 25m
3 stops
$788Multiple Airlines
Sat, Jun 20 - Sun, Jul 5
Delta Logo
10:30 pm - 8:00 pm
PDX
-
KIN
19h 30m
1 stop
Delta Logo
9:00 am - 8:39 am
KIN
-
PDX
25h 39m
2 stops
$884Delta
Mon, Jun 8 - Tue, Jun 16
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Air Canada Logo
3:05 pm - 11:03 pm
KIN
-
PDX
33h 58m
2 stops
$886Air Canada
Mon, Jun 8 - Tue, Jun 16
Multiple Airlines Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Multiple Airlines Logo
3:05 pm - 1:50 pm
KIN
-
PDX
24h 45m
3 stops
$929Multiple Airlines
Booking Insights

KAYAK's insights & trends for Portland to Jamaica flights

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Jamaica, 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 Jamaica is March, when tickets cost $224 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $638 and $581 respectively.

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

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 Jamaica, 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 Jamaica, you should book around 3 weeks before departure, which saves you about 61% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$172
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Portland to Montego Bay

FAQs - booking Jamaica flights

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

    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 Jamaica.

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

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

    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 Jamaica 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 Jamaica?

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

Reviews of the top 3 airlines serving from Portland to Jamaica

 
Need help choosing which airline to fly with from Portland to Jamaica? 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 8444 reviews
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
7.8Comfort
Airline reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

10.0 Excellentangela, May 2026
LGA - PBI
Read more Delta reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

This flight is a quick way to get to Chicago, but a bit expensive.

Very comfortable seating and the Flight staff were very attentive. The premium economy section that I was seated in was very clean, updated, and well appointed. I would highly recommend flying United Airlines as this experience was better than the Japan Airlines business class that I flew several months ago.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Our flight to Rome, Italy was cancelled the day of and we were never informed. We only found out because I was trying to get into my husbands account and called to get his account number. Had to pay more for worse seating on another airline.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

First class ticket gets you no seat back entertainment? I have to bring my own laptop to see a movie? And most of their movies have ADS? No thank you. Worse: Tiny snacks only on a 2 hr flight?

Cancelled flight. Still waiting to get home for grand daughter’s graduation .

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

Everything you need to know for your flight from Portland to Jamaica

Information on your arrival and departure airports