$138 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 5/5. 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$349
Kingston
Kingston1 stop$472
Montego Bay
Montego Bay2 stops$349
Kingston
Kingston1 stop$472

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

Tue, Apr 28 - Sat, May 2
United Airlines Logo
6:04 am - 3:10 pm
PWM
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MBJ
10h 06m
2 stops
United Airlines Logo
4:12 pm - 10:23 am
MBJ
-
PWM
17h 11m
2 stops
$349United Airlines
Tue, Jun 30 - Thu, Jul 2
American Airlines Logo
5:57 pm - 11:45 am
PWM
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MBJ
18h 48m
2 stops
American Airlines Logo
2:31 pm - 10:31 am
MBJ
-
PWM
19h 00m
2 stops
$357American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:46 pm - 1:58 pm
PWM
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MBJ
20h 12m
1 stop
American Airlines Logo
5:13 pm - 11:13 am
MBJ
-
PWM
17h 00m
2 stops
$363American Airlines
Tue, Oct 6 - Tue, Nov 3
United Airlines Logo
6:00 am - 11:43 am
PWM
-
MBJ
6h 43m
1 stop
United Airlines Logo
3:36 pm - 10:57 pm
MBJ
-
PWM
7h 21m
1 stop
$370United Airlines
Tue, May 5 - Wed, Aug 5
United Airlines Logo
6:00 am - 11:43 am
PWM
-
MBJ
6h 43m
1 stop
United Airlines Logo
4:12 pm - 11:51 pm
MBJ
-
PWM
6h 39m
1 stop
$387United Airlines
Tue, Oct 6 - Tue, Nov 3
American Airlines Logo
7:20 pm - 11:00 am
PWM
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MBJ
16h 40m
2 stops
American Airlines Logo
11:15 am - 11:38 pm
MBJ
-
PWM
12h 23m
2 stops
$399American Airlines
Tue, Apr 28 - Sat, May 2
American Airlines Logo
7:10 am - 1:19 pm
PWM
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MBJ
7h 09m
1 stop
American Airlines Logo
12:56 pm - 9:54 am
MBJ
-
PWM
19h 58m
2 stops
$401American Airlines
Mon, Sep 14 - Thu, Sep 17
JetBlue Logo
6:00 am - 12:58 pm
PWM
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MBJ
7h 58m
1 stop
JetBlue Logo
3:00 pm - 11:52 pm
MBJ
-
PWM
7h 52m
1 stop
$439JetBlue
Tue, May 26 - Tue, Jun 2
JetBlue Logo
2:36 pm - 10:48 pm
PWM
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KIN
9h 12m
1 stop
JetBlue Logo
12:20 pm - 11:58 pm
KIN
-
PWM
10h 38m
1 stop
$472JetBlue
Tue, May 12 - Tue, May 19
Delta Logo
2:05 pm - 8:00 pm
PWM
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KIN
6h 55m
1 stop
Delta Logo
9:00 am - 12:43 am
KIN
-
PWM
14h 43m
2 stops
$566Delta
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 ($357) and United Airlines ($370).

Good to know

Low seasonApril
Cheapest flight$138
Best time to beat the crowds with an average 24% drop 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.
7.9
DeltaOverall score based on 8409 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

6.0 GoodAnonymous, Apr 2026
DTW - AMS
Read more Delta reviews

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

Vegetarian selection could be better. Bread was too hard to chew.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

Overall flight was ok. Flight attendant was receptive to assisting passengers with tight connections.

Checking in united could not figure out my star alliance gold. Baggage did not get marked priority and didn't receive boarding passes. When got to SFO lounge personal fixed everything Immediately

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

American Airlines is a miserable experience. It is predictably miserable, in the sense that every time I fly American, I brace myself for the certainty that it will be unpleasant and uncomfortable. But it is unpredictable in the sense that I never know if the flight will be on time or delayed nine hours (both happened to me this week). I never know if I will be able to sit in the seat that I selected when I purchased the ticket or if I will be told by Customer Service (!!!) that I must relocate from first class to a seat in the back of the aircraft with no explanation (both happened to me this week). Will the food be frozen and half defrosted, or scalding hot? Will the drinks be warm? Will the flight attendants be surly and mean? Will the toilets be cramped and foul? Will the seats be narrow and uncomfortable? Will there be a real electric outlet at the seat, or just an unreliable USB-2 port? Will there be enough seats in the boarding lounge or just a few? Will the boarding process be smooth and efficient, or will the gate agents mess it up and delay it needlessly for 30 or 40 minutes? Will the catering and cleaning crew be prompt or will they take an extra 30 minutes? Will the brakes on the aircraft work properly, or will the pilot delay takeoff for four hours while the ground crew attends to what can only be described as routine maintenance that should have been done the night before? I've eexperienced every one of these unpleasant things this year, 2026. The only thing I can reliably count on is that American will find a new way to make the experience of flying as miserable as they possibly can.

Flight was fine, but not having WiFi was a major negative

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Wifi was spotty. Tray table was very dirty when I sat down.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

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

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