$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 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$432
Kingston
Kingston2 stops$694
Montego Bay
Montego Bay1 stop$432
Kingston
Kingston2 stops$694

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
11:34 pm - 1:12 pm
PDX
-
MBJ
11h 38m
1 stop
American Airlines Logo
2:12 pm - 11:59 pm
MBJ
-
PDX
11h 47m
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, Sep 1 - Sat, Sep 5
JetBlue Logo
2:19 pm - 12:45 pm
PDX
-
KIN
20h 26m
2 stops
JetBlue Logo
1:55 pm - 1:04 pm
KIN
-
PDX
25h 09m
2 stops
$694JetBlue
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
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
$774Air Canada
Fri, Sep 11 - Tue, Sep 15
United Airlines Logo
8:25 am - 1:54 pm
PDX
-
KIN
27h 29m
2 stops
United Airlines Logo
2:57 pm - 10:52 pm
KIN
-
PDX
33h 55m
2 stops
$807United Airlines
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
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
Sun, Oct 25 - Wed, Oct 28
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 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 8456 reviews
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
7.8Comfort
Airline reviews

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.

6.0 GoodAnonymous, May 2026
PDX - MSP
Read more Delta reviews

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.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

My seat had no padding, it was literally plywood with a plastic cover. I could not change seats on my 10 hour flight. My excitement for this trip helped me deal with the pain.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

It was terrible! Two hour delays, poor in flight service, made us check our carry on even though there was plenty of overhead storage

Boarding was good, was able to get on early and get settled in . Loved the glass of wine before take off. Once in the air the service was amazing, from the snacks, drinks and the food was good. The flight attendants were very good and attentive. Love flying with Delta..

The flights were on time- Great service Would have liked more options for food choices.

The brakes on the A220 are sensitive and uncomfortably grabby

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

We had a 90 minute delay due to equipment failure that was detected just before we took off. United rebooked my connecting flight.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

This was a Lufthansa flight. Disappointing main meal. Very rough over Canada and arrival at FRA. IFE was almost unusable.

Poor seating comfort, seat cushion too thin, very uncomfortable. My luggage didi not make the flight due to equipment change. At least. United had it delivered the next day. I was without my toilet items for one day.

Flight cancelled because of the grounded 737s. United was good about it and got us onto a later Alaska Airlines flight to Oakland (not San Francisco as originally intended). Had to go through security again and my wife dropped her MacBook Pro, which broke, a $2,500 whoopsie. But we made it home.

I liked being upgraded to first class. The flight was a redeye, so I did sleep most of it.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We were told there would be no food/beverage service due to turbulence. There was very little turbulence on the 2+ hour flight. I was in First Class and thought they could have done a quick service after take off as they had a quite bit of time before we would be reaching the predicted turbulent area. They could have at least passed out a quick bag of pretzels.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

I love the Kayak has keep on updating me about flight status as it was delayed for 30mins. as well notifications to book seat and if any change on booking. Tickets were also cheap compared to British Airways online website. No hidden charges or terms n conditions. Keep it up!!!

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

Information on your arrival and departure airports