$221 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 4/29. 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$357
Kingston
Kingston1 stop$485
Montego Bay
Montego Bay2 stops$357
Kingston
Kingston1 stop$485

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, May 17 - Sat, May 23
American Airlines Logo
6:00 am - 3:37 pm
PWM
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MBJ
10h 37m
2 stops
American Airlines Logo
12:41 pm - 9:38 am
MBJ
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PWM
19h 57m
2 stops
$357American Airlines
Wed, Apr 29 - Sat, May 2
American Airlines Logo
6:00 am - 1:25 pm
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MBJ
8h 25m
2 stops
American Airlines Logo
12:56 pm - 9:54 am
MBJ
-
PWM
19h 58m
2 stops
$362American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:50 pm - 1:58 pm
PWM
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MBJ
20h 08m
1 stop
American Airlines Logo
3:20 pm - 11:34 am
MBJ
-
PWM
19h 14m
2 stops
$363American Airlines
Wed, Apr 29 - Sat, May 2
American Airlines Logo
7:10 am - 1:25 pm
PWM
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MBJ
7h 15m
1 stop
American Airlines Logo
3:20 pm - 11:26 pm
MBJ
-
PWM
7h 06m
1 stop
$396American Airlines
Sun, May 17 - Sat, May 23
JetBlue Logo
6:00 am - 1:00 pm
PWM
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MBJ
8h 00m
1 stop
JetBlue Logo
2:23 pm - 11:56 pm
MBJ
-
PWM
8h 33m
1 stop
$398JetBlue
Tue, May 19 - Sun, May 24
American Airlines Logo
6:00 am - 2:15 pm
PWM
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MBJ
9h 15m
1 stop
American Airlines Logo
5:17 pm - 1:38 pm
MBJ
-
PWM
19h 21m
2 stops
$401American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
6:50 pm - 1:58 pm
PWM
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MBJ
20h 08m
1 stop
American Airlines Logo
3:20 pm - 11:12 am
MBJ
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PWM
18h 52m
2 stops
$403American Airlines
Wed, Apr 29 - Sun, May 3
American Airlines Logo
7:10 am - 1:25 pm
PWM
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MBJ
7h 15m
1 stop
American Airlines Logo
4:37 pm - 11:15 am
MBJ
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PWM
17h 38m
2 stops
$406American Airlines
Sat, May 23 - Mon, Jun 1
American Airlines Logo
5:57 pm - 1:08 pm
PWM
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MBJ
20h 11m
2 stops
American Airlines Logo
2:08 pm - 10:32 am
MBJ
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PWM
19h 24m
2 stops
$407American Airlines
Sat, May 23 - Mon, Jun 1
JetBlue Logo
2:19 pm - 10:45 pm
PWM
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KIN
9h 26m
1 stop
JetBlue Logo
12:18 pm - 11:56 pm
KIN
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PWM
10h 38m
1 stop
$485JetBlue
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.

Which airlines provide the cheapest flights from Portland to Jamaica?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Jamaica were found on American Airlines ($362) and JetBlue ($419).

Good to know

Low seasonMay
Cheapest flight$157
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 13% 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.
7.9
DeltaOverall score based on 8288 reviews
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

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

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

Not really sure I enjoyed the flight at all. The flight attendants seemed a little tired and rude at times. The snacks were lacking in taste and sustenance. The flight was incredibly turbulent for three plus hours and the pilot had to do a second pass to land at our final destination because he was coming in so fast. He must have taken a short cut and because of it we had to suffer the violent turbulence and the dropping down. It had to be one of if not the worse flights I have ever been on and have traveled vastly all over the world.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

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

Information on your arrival and departure airports