$148 Find Cheap Flights from Portland to Jamaica - Compare and Save

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 12/8. 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 Bay1 stop$352
Kingston
Kingston1 stop$515
Montego Bay
Montego Bay1 stop$352
Kingston
Kingston1 stop$515

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 30 - Sat, Dec 5
Delta Logo
6:00 am - 2:15 pm
PWM
-
MBJ
8h 15m
1 stop
Delta Logo
2:20 pm - 10:23 pm
MBJ
-
PWM
8h 03m
1 stop
$352Delta
Mon, Nov 30 - Fri, Dec 4
Delta Logo
6:00 am - 12:55 pm
PWM
-
MBJ
6h 55m
1 stop
Delta Logo
2:20 pm - 11:53 am
MBJ
-
PWM
21h 33m
2 stops
$357Delta
Mon, Nov 30 - Sun, Dec 6
Delta Logo
6:00 am - 2:15 pm
PWM
-
MBJ
8h 15m
1 stop
Delta Logo
2:20 pm - 10:23 pm
MBJ
-
PWM
8h 03m
1 stop
$406Delta
Thu, Nov 26 - Sat, Dec 5
Delta Logo
3:00 pm - 12:55 pm
PWM
-
MBJ
21h 55m
2 stops
Delta Logo
6:00 pm - 11:53 am
MBJ
-
PWM
17h 53m
2 stops
$411Delta
Fri, Sep 4 - Fri, Sep 11
United Airlines Logo
6:53 pm - 11:43 am
PWM
-
MBJ
17h 50m
1 stop
United Airlines Logo
12:52 pm - 9:08 am
MBJ
-
PWM
19h 16m
1 stop
$437United Airlines
Fri, Nov 27 - Mon, Dec 7
Delta Logo
4:50 pm - 4:35 pm
PWM
-
MBJ
23h 45m
2 stops
Delta Logo
6:00 pm - 9:30 am
MBJ
-
PWM
15h 30m
2 stops
$451Delta
Fri, Sep 4 - Fri, Sep 11
United Airlines Logo
7:35 pm - 11:43 am
PWM
-
MBJ
17h 08m
2 stops
United Airlines Logo
12:52 pm - 9:08 am
MBJ
-
PWM
19h 16m
1 stop
$482United Airlines
Tue, Oct 27 - Fri, Oct 30
JetBlue Logo
6:30 am - 3:58 pm
PWM
-
KIN
10h 28m
1 stop
JetBlue Logo
10:09 am - 11:43 pm
KIN
-
PWM
12h 34m
1 stop
$515JetBlue
Tue, Oct 27 - Fri, Oct 30
JetBlue Logo
6:30 am - 3:58 pm
PWM
-
KIN
10h 28m
1 stop
JetBlue Logo
10:09 am - 11:43 pm
KIN
-
PWM
12h 34m
1 stop
$689JetBlue
Fri, Aug 7 - Sun, Aug 9
American Airlines Logo
6:02 am - 7:42 pm
PWM
-
KIN
14h 40m
2 stops
American Airlines Logo
6:05 am - 11:37 pm
KIN
-
PWM
16h 32m
2 stops
$839American Airlines
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 May, when tickets cost $352 (return) on average. On the other hand, the most expensive months are September and July, when the average cost of round-trip tickets is $715 and $704 respectively.

Good to know

Low season

March

Cheapest flight

$148
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly with an average 16% 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.

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 8476 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

10.0 ExcellentAnonymous, Jul 2026
DTW - ATL
Read more Delta reviews

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

The Atlanta airport had thunderstorms, which caused our flight to be delayed by multiple hours. Once we were able to board.the gate agent was rude and was trying to rush us onto the plane because the team in the plane was about to run out of hours once we were all aboard the plane they ran into an issue where the catering truck was filling up the back of the plane and they left and had to come back because they didn’t fill it up all the way, causing even more of a delay. My seat was very tight. I didn’t have a lot of legroom overall this was a miserable experience.

Flight delayed due to ground hold. Republic airways did a great job.

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..

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Flight was delayed nearly one hour. Just because of Deltas poor management. Was so late reached home after midnight .

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Why is it that United flights from Newark are constantly delayed? Newark is a United hub!!!!!

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Very good, boarded and took off on time and landed early

It was good overall but when I book my flight and seat through Kayak, AA will at times change those seats during check-in time which I don’t understand why. I always book aisle seats and had to sit at window for my flight to Austin this trip.

Mostly great. Only issue was with the WiFi. Halfway through the flight it was spotty and I was unable to work as I planned. This impacted my work products as I am traveling for business and it was an unexpected hindrance which was inconvenient. Flight here was amazing. For a 5 hour flight something more than a Biscoff would be nice but I’m just swinging at windmills I guess…

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Nothing exceptional. No drink of any type, even in first class was provided for the hour and half trip.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

I just for my TSA. So security line is short and upgraded to one group up. I do think the ground crew should learn new way of boarding - the passengers sitting in higher number seat should board first to prevent traffic jam.

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

Information on your arrival and departure airports