$192 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 8/10. 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 21% 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$432
Kingston
Kingston2 stops$714
Montego Bay
Montego Bay1 stop$432
Kingston
Kingston2 stops$714

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 - Tue, Nov 10
American Airlines Logo
10:45 pm - 12:55 pm
PDX
-
MBJ
11h 10m
1 stop
American Airlines Logo
4:05 pm - 11:51 pm
MBJ
-
PDX
10h 46m
1 stop
$432American Airlines
Mon, Nov 2 - Tue, Nov 10
Delta Logo
5:05 pm - 12:25 pm
PDX
-
MBJ
16h 20m
2 stops
Delta Logo
6:00 pm - 9:16 am
MBJ
-
PDX
18h 16m
2 stops
$437Delta
Mon, Nov 2 - Wed, Nov 11
American Airlines Logo
10:45 pm - 12:55 pm
PDX
-
MBJ
11h 10m
1 stop
American Airlines Logo
4:02 pm - 10:59 pm
MBJ
-
PDX
9h 57m
1 stop
$473American Airlines
Tue, Oct 27 - Tue, Nov 10
American Airlines Logo
6:33 pm - 9:05 am
PDX
-
MBJ
12h 32m
2 stops
American Airlines Logo
4:05 pm - 10:58 am
MBJ
-
PDX
21h 53m
2 stops
$478American Airlines
Tue, Oct 13 - Tue, Oct 20
Delta Logo
10:05 pm - 11:25 am
PDX
-
MBJ
11h 20m
1 stop
Delta Logo
1:32 pm - 10:26 pm
MBJ
-
PDX
10h 54m
1 stop
$561Delta
Wed, Sep 16 - Mon, Sep 21
Air Canada Logo
10:10 am - 10:25 am
PDX
-
KIN
22h 15m
2 stops
Air Canada Logo
3:05 pm - 2:46 pm
KIN
-
PDX
25h 41m
2 stops
$714Air Canada
Sat, Sep 19 - Wed, Sep 23
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Air Canada Logo
3:05 pm - 2:46 pm
KIN
-
PDX
25h 41m
2 stops
$747Air Canada
Thu, Aug 6 - Thu, Aug 13
United Airlines Logo
11:59 pm - 1:54 pm
PDX
-
KIN
35h 55m
2 stops
United Airlines Logo
2:56 pm - 8:10 pm
KIN
-
PDX
31h 14m
2 stops
$811United Airlines
Thu, Jul 16 - Wed, Jul 22
United Airlines Logo
11:59 pm - 1:54 pm
PDX
-
KIN
35h 55m
2 stops
United Airlines Logo
2:56 pm - 9:25 am
KIN
-
PDX
20h 29m
2 stops
$854United Airlines
Tue, Jul 28 - Fri, Jul 31
JetBlue Logo
2:16 pm - 10:58 am
PDX
-
KIN
18h 42m
2 stops
JetBlue Logo
9:45 pm - 10:31 pm
KIN
-
PDX
26h 46m
2 stops
$863JetBlue
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 October and July, when the average cost of round-trip tickets is $512 and $508 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 56% 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$192
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 4% 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.
7.8
DeltaOverall score based on 8432 reviews
7.8Comfort
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

2.0 MediocreHu, Jun 2026
AUS - JFK
Read more Delta reviews

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

We used Kayak to reserve our tickets and specifically checked the luggage option which was a more expensive option. When we arrived at the terminal we had to pay an extra $90 per suitcase for the three passengers. This has been a pattern for the past 3 years. Why charge for a more expensive luggage option, and the ticket price not include luggage?

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

American Airlines is a great dependable airline, on time arrival and departure with polite crew and staff.

I think since I am an AA Advantage member, my checked bags should have been free, but I paid for all 4 of us.

This flight moved Gates several times in a short time period, from B to C, which required a substantial walk or rail ride. Then the flight was delayed more than 2 hours and the food was subpar compared to other flights.

Flight was delayed multiple times without giving any particular reason and the only thing that was communicated was that 'Aircraft is getting ready'. I was stuck at SFO airport for 15 hours and finally took Southwest Airlines flight back home to Dallas.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

I was not clear if food was offered or not.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

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

Information on your arrival and departure airports