$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 10/31. 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 Jamaica

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$703
Montego Bay
Montego Bay1 stop$392
Kingston
Kingston2 stops$703

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

Mon, Nov 2 - Wed, Nov 11
American Airlines Logo
10:45 pm - 10:15 am
PDX
-
MBJ
8h 30m
1 stop
American Airlines Logo
11:09 am - 9:15 pm
MBJ
-
PDX
13h 06m
1 stop
$392American Airlines
Mon, Nov 2 - Wed, Nov 11
American Airlines Logo
5:42 pm - 10:15 am
PDX
-
MBJ
13h 33m
2 stops
American Airlines Logo
11:09 am - 9:15 pm
MBJ
-
PDX
13h 06m
1 stop
$397American Airlines
Tue, Sep 29 - Sun, Oct 4
United Airlines Logo
4:07 pm - 11:43 am
PDX
-
MBJ
17h 36m
2 stops
United Airlines Logo
2:40 pm - 10:49 pm
MBJ
-
PDX
10h 09m
1 stop
$407United Airlines
Mon, Nov 2 - Tue, Nov 10
Delta Logo
7:14 pm - 12:25 pm
PDX
-
MBJ
14h 11m
2 stops
Delta Logo
6:00 pm - 9:31 am
MBJ
-
PDX
18h 31m
2 stops
$427Delta
Tue, Sep 29 - Sun, Oct 4
United Airlines Logo
6:45 pm - 11:43 am
PDX
-
MBJ
14h 58m
2 stops
United Airlines Logo
2:40 pm - 9:30 am
MBJ
-
PDX
20h 50m
2 stops
$458United Airlines
Tue, Oct 13 - Tue, Oct 20
American Airlines Logo
10:44 pm - 9:05 am
PDX
-
MBJ
8h 21m
1 stop
American Airlines Logo
5:00 pm - 10:57 am
MBJ
-
PDX
19h 57m
2 stops
$517American Airlines
Sat, Sep 26 - Wed, Sep 30
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Air Canada Logo
3:05 pm - 7:06 pm
KIN
-
PDX
30h 01m
2 stops
$703Air Canada
Thu, Oct 8 - Fri, Oct 16
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
16h 10m
2 stops
Air Canada Logo
3:05 pm - 2:51 pm
KIN
-
PDX
25h 46m
2 stops
$727Air Canada
Sun, Jul 19 - Wed, Jul 22
Multiple Airlines Logo
7:45 pm - 5:10 pm
PDX
-
KIN
19h 25m
3 stops
Multiple Airlines Logo
3:05 pm - 7:11 pm
KIN
-
PDX
30h 06m
2 stops
$878Multiple Airlines
Sat, Oct 10 - Sat, Oct 17
Delta Logo
6:04 am - 7:30 pm
PDX
-
KIN
11h 26m
1 stop
Delta Logo
9:00 am - 7:08 pm
KIN
-
PDX
12h 08m
1 stop
$894Delta
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 August, when the average cost of round-trip tickets is $638 and $638 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 4 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.
8.0
SouthwestOverall score based on 4298 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

I'm glad it wasn't only 75% full because I could get a good seat

8.0 ExcellentBobby, May 2026
BNA - GSP
Read more Southwest reviews

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

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.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

The small flights with Valet Luggage has a poor service

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

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

Information on your arrival and departure airports