$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 4/27. 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 Bay2 stops$397
Kingston
Kingston2 stops$747
Montego Bay
Montego Bay2 stops$397
Kingston
Kingston2 stops$747

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, May 1 - Mon, May 4
United Airlines Logo
11:55 pm - 3:10 pm
PDX
-
MBJ
13h 15m
2 stops
United Airlines Logo
2:40 pm - 9:38 am
MBJ
-
PDX
20h 58m
2 stops
$397United Airlines
Fri, May 29 - Wed, Jun 3
Delta Logo
3:30 pm - 11:26 am
PDX
-
MBJ
17h 56m
2 stops
Delta Logo
4:59 pm - 11:46 am
MBJ
-
PDX
20h 47m
2 stops
$427Delta
Fri, May 1 - Mon, May 4
United Airlines Logo
11:55 pm - 12:50 pm
PDX
-
MBJ
10h 55m
1 stop
United Airlines Logo
2:40 pm - 10:59 pm
MBJ
-
PDX
10h 19m
1 stop
$451United Airlines
Fri, Jul 3 - Sat, Jul 11
United Airlines Logo
10:40 pm - 1:30 pm
PDX
-
MBJ
12h 50m
2 stops
United Airlines Logo
12:52 pm - 9:15 pm
MBJ
-
PDX
10h 23m
1 stop
$456United Airlines
Fri, Sep 11 - Sat, Sep 19
United Airlines Logo
10:50 pm - 11:43 am
PDX
-
MBJ
10h 53m
1 stop
United Airlines Logo
2:40 pm - 9:29 am
MBJ
-
PDX
20h 49m
2 stops
$478United Airlines
Tue, May 26 - Sun, May 31
United Airlines Logo
10:52 pm - 11:43 am
PDX
-
MBJ
10h 51m
1 stop
United Airlines Logo
4:33 pm - 10:20 am
MBJ
-
PDX
19h 47m
2 stops
$483United Airlines
Fri, Sep 4 - Wed, Sep 9
Multiple Airlines Logo
2:20 pm - 8:32 pm
PDX
-
KIN
28h 12m
2 stops
Multiple Airlines Logo
3:05 pm - 7:06 pm
KIN
-
PDX
30h 01m
2 stops
$787Multiple Airlines
Wed, Jul 1 - Tue, Jul 7
JetBlue Logo
2:20 pm - 8:32 pm
PDX
-
KIN
28h 12m
2 stops
JetBlue Logo
9:57 pm - 1:04 pm
KIN
-
PDX
17h 07m
2 stops
$854JetBlue
Wed, Jul 1 - Tue, Jul 7
JetBlue Logo
2:20 pm - 8:32 pm
PDX
-
KIN
28h 12m
2 stops
JetBlue Logo
9:57 pm - 1:04 pm
KIN
-
PDX
17h 07m
2 stops
$861JetBlue
Wed, Jul 22 - Thu, Aug 20
Air Canada Logo
7:45 pm - 1:55 pm
PDX
-
KIN
40h 10m
2 stops
Air Canada Logo
11:35 am - 9:31 am
KIN
-
PDX
23h 56m
2 stops
$897Air Canada
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 February, when tickets cost $626 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $990 and $881 respectively.

Good to know

Low seasonAugust
Cheapest flight$172
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 7% 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 4333 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

10.0 ExcellentGwen, Mar 2026
DAL - BNA
Read more Southwest reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

We had excellent customer service despite the chaos at George Bush airport in Houston!

It isvvery small flight. No leg room . No space to put my personal item at feet.

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

No seat back entertainment. And app had a hard time getting entertainment loaded.

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Delays with no explanation. It could have been handled better.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.

I appreciate that I finally got the seat I paid extra for this time. Thank you

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

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

Information on your arrival and departure airports