$256 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 11/24. 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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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 Bay2 stops$619
Kingston
Kingston2 stops$695
Montego Bay
Montego Bay2 stops$619
Kingston
Kingston2 stops$695

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

Tue, Feb 3 - Wed, Feb 11
Air Canada Logo
9:50 am - 1:10 pmPDX-MBJ
24h 20m2 stops
Air Canada Logo
7:05 pm - 2:40 pmMBJ-PDX
22h 35m2 stops
$619Air Canada
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Tue, Feb 3 - Wed, Feb 11
Air Canada Logo
7:00 pm - 1:10 pmPDX-MBJ
15h 10m2 stops
Air Canada Logo
7:05 pm - 9:15 amMBJ-PDX
41h 10m2 stops
$627Air Canada
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Wed, Dec 10 - Thu, Dec 25
Delta Logo
10:10 pm - 4:33 pmPDX-MBJ
15h 23m1 stop
Delta Logo
8:00 am - 6:53 pmMBJ-PDX
13h 53m1 stop
$639Delta
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Tue, Dec 9 - Thu, Dec 25
Delta Logo
12:32 am - 4:33 pmPDX-MBJ
13h 01m2 stops
Delta Logo
1:57 pm - 11:21 pmMBJ-PDX
12h 24m1 stop
$644Delta
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Fri, Jan 30 - Mon, Feb 2
Air Canada Logo
7:00 pm - 1:10 pmPDX-MBJ
15h 10m2 stops
Air Canada Logo
5:45 pm - 2:40 pmMBJ-PDX
23h 55m2 stops
$649Air Canada
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Wed, Dec 17 - Wed, Dec 24
United Airlines Logo
11:59 pm - 1:46 pmPDX-MBJ
10h 47m1 stop
United Airlines Logo
3:20 pm - 1:20 pmMBJ-PDX
25h 00m1 stop
$653United Airlines
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Sat, Dec 13 - Sat, Dec 20
American Airlines Logo
10:45 pm - 10:13 amPDX-MBJ
8h 28m1 stop
American Airlines Logo
11:07 am - 12:59 amMBJ-PDX
16h 52m1 stop
$664American Airlines
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Sat, Dec 13 - Sun, Dec 21
American Airlines Logo
10:15 pm - 10:12 amPDX-MBJ
8h 57m1 stop
American Airlines Logo
2:23 pm - 12:59 amMBJ-PDX
13h 36m1 stop
$669American Airlines
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Thu, Dec 18 - Thu, Dec 25
United Airlines Logo
11:59 pm - 2:05 pmPDX-MBJ
11h 06m1 stop
United Airlines Logo
3:20 pm - 10:59 pmMBJ-PDX
10h 39m1 stop
$678United Airlines
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Mon, Dec 22 - Fri, Dec 26
Southwest Logo
9:00 pm - 2:55 pmPDX-MBJ
14h 55m2 stops
Southwest Logo
3:25 pm - 1:05 amMBJ-PDX
12h 40m2 stops
$893Southwest
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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 August, when tickets cost $705 (return) on average. On the other hand, the most expensive months are October and September, when the average cost of round-trip tickets is $1,099 and $848 respectively.

What’s the cheapest day of the week to fly from Portland to Jamaica?

The average price of all round-trip flights from Portland to Jamaica clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Portland to Jamaica, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Jamaica, Wednesday is the cheapest day to fly and Friday is the most expensive.

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 4 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$256
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% increase in price.
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.

  • What is the cheapest time of day to fly to Jamaica?

    The cheapest time of day to fly to Jamaica is generally in the afternoon, when round-trip flights cost $571 on average. Morning departures are around 17% cheaper than evening flights, on average. The most expensive time of day to fly to Jamaica is generally in the evening, which is peak travel time and where the average cost of a ticket is $789.

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 4239 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

Premium Plus is a really good idea for longer flights

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

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

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