$241 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 11/30. 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$370
Kingston
Kingston2 stops$454
Montego Bay
Montego Bay1 stop$370
Kingston
Kingston2 stops$454

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

Sun, Jan 4 - Sun, Jan 11
Delta Logo
5:45 am - 12:58 pmPWM-MBJ
7h 13m1 stop
Delta Logo
8:00 am - 10:29 pmMBJ-PWM
14h 29m1 stop
$370Delta
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Sun, Dec 7 - Fri, Dec 12
United Airlines Logo
6:00 am - 2:29 pmPWM-MBJ
8h 29m1 stop
United Airlines Logo
3:36 pm - 11:09 pmMBJ-PWM
7h 33m1 stop
$389United Airlines
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Mon, Feb 9 - Fri, Feb 13
Delta Logo
5:30 am - 12:54 pmPWM-MBJ
7h 24m1 stop
Delta Logo
4:40 pm - 12:30 pmMBJ-PWM
19h 50m2 stops
$394Delta
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Sun, Jan 4 - Sun, Jan 11
American Airlines Logo
5:20 pm - 12:25 pmPWM-MBJ
19h 05m2 stops
American Airlines Logo
4:43 pm - 12:05 pmMBJ-PWM
19h 22m2 stops
$399American Airlines
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Sun, Jan 4 - Sun, Jan 11
Delta Logo
5:45 am - 8:41 pmPWM-MBJ
14h 56m1 stop
Delta Logo
12:38 pm - 12:20 amMBJ-PWM
11h 42m2 stops
$410Delta
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Mon, Feb 2 - Tue, Feb 10
Delta Logo
6:00 am - 3:20 pmPWM-MBJ
9h 20m2 stops
Delta Logo
2:00 pm - 12:20 amMBJ-PWM
10h 20m1 stop
$429Delta
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Thu, Dec 18 - Thu, Dec 25
United Airlines Logo
7:30 pm - 4:12 pmPWM-MBJ
20h 42m1 stop
United Airlines Logo
3:55 pm - 11:22 pmMBJ-PWM
7h 27m1 stop
$434United Airlines
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Mon, Dec 22 - Mon, Dec 29
American Airlines Logo
6:41 pm - 12:22 pmPWM-MBJ
17h 41m2 stops
American Airlines Logo
1:12 pm - 10:55 pmMBJ-PWM
9h 43m1 stop
$489American Airlines
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Tue, Feb 24 - Thu, Feb 26
American Airlines Logo
7:00 am - 8:44 pmPWM-KIN
13h 44m2 stops
American Airlines Logo
11:09 am - 12:12 pmKIN-PWM
25h 03m2 stops
$528American Airlines
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Mon, Dec 22 - Mon, Dec 29
American Airlines Logo
5:20 pm - 10:21 amPWM-MBJ
17h 01m2 stops
American Airlines Logo
6:05 pm - 12:11 pmMBJ-PWM
18h 06m2 stops
$553American Airlines
Find Deal
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 September, when tickets cost $465 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $1,215 and $725 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.

When flying from Portland to Jamaica, you should consider leaving on a Friday and avoid Tuesdays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

Good to know

Low seasonJuly
Cheapest flight$157
Most popular time to fly with an average 96% 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 evening, when round-trip flights cost $370 on average. Morning departures are around 76% more expensive than evening flights, on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $650.

Reviews of the top 5 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 4238 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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.

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

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

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!

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

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.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

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

Information on your arrival and departure airports