$138 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 9/19. 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$362
Kingston
Kingston2 stops$439
Montego Bay
Montego Bay1 stop$362
Kingston
Kingston2 stops$439

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

Wed, Sep 9 - Thu, Sep 17
Delta Logo
6:02 am - 11:34 am
PWM
-
MBJ
6h 32m
1 stop
Delta Logo
12:59 pm - 11:56 pm
MBJ
-
PWM
9h 57m
1 stop
$362Delta
Thu, Oct 1 - Sat, Oct 10
Delta Logo
6:00 am - 3:34 pm
PWM
-
MBJ
10h 34m
1 stop
Delta Logo
12:50 pm - 12:10 am
MBJ
-
PWM
10h 20m
1 stop
$411Delta
Thu, Aug 20 - Thu, Aug 27
Delta Logo
6:30 am - 8:13 pm
PWM
-
KIN
14h 43m
2 stops
Delta Logo
9:13 am - 11:13 pm
KIN
-
PWM
13h 00m
1 stop
$439Delta
Thu, Oct 1 - Sun, Oct 11
Delta Logo
6:30 am - 3:34 pm
PWM
-
MBJ
10h 04m
2 stops
Delta Logo
12:50 pm - 12:10 am
MBJ
-
PWM
10h 20m
1 stop
$463Delta
Wed, Sep 9 - Thu, Sep 17
American Airlines Logo
6:00 pm - 12:53 pm
PWM
-
MBJ
19h 53m
2 stops
American Airlines Logo
1:54 pm - 10:03 am
MBJ
-
PWM
19h 09m
2 stops
$514American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
5:30 am - 2:23 pm
PWM
-
MBJ
9h 53m
1 stop
American Airlines Logo
2:52 pm - 10:31 am
MBJ
-
PWM
18h 39m
2 stops
$517American Airlines
Thu, Oct 1 - Sun, Oct 11
United Airlines Logo
7:25 pm - 11:43 am
PWM
-
MBJ
41h 18m
2 stops
United Airlines Logo
2:40 pm - 11:59 pm
MBJ
-
PWM
32h 19m
2 stops
$541United Airlines
Thu, Oct 1 - Sun, Oct 11
United Airlines Logo
6:00 am - 11:43 am
PWM
-
MBJ
6h 43m
1 stop
United Airlines Logo
12:52 pm - 11:28 pm
MBJ
-
PWM
9h 36m
1 stop
$548United Airlines
Sat, Oct 3 - Sat, Oct 10
JetBlue Logo
6:00 am - 9:00 am
PWM
-
KIN
28h 00m
1 stop
JetBlue Logo
5:30 pm - 11:52 pm
KIN
-
PWM
29h 22m
1 stop
$688JetBlue
Sat, Oct 3 - Sat, Oct 10
JetBlue Logo
6:00 am - 10:50 am
PWM
-
KIN
29h 50m
2 stops
JetBlue Logo
1:53 pm - 11:52 pm
KIN
-
PWM
8h 59m
2 stops
$696JetBlue
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 $0 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $634 and $559 respectively.

Good to know

Low seasonMay
Cheapest flight$138
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 17% 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 8451 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

8.0 ExcellentAnonymous, Jul 2026
DTW - MBS
Read more Delta reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

MSY had lots of coffee/breakfast options for morning flights. Bathrooms were clean. Lots of filling stations for water bottles. Delta flight was on time. The plane was clean. The staff was friendly and efficient.

London to Atlanta was good. Atlanta to Phoenix was not. Poor boarding as I had to check my rollerboard even though there was plenty of room in the bins. Crew seemed inexperienced. Sat just off the gate for nearly 30 minutes with no explanation from the pilot while the cabin got hot. I typically have a much better experience with Delta.

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

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 .

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

It's fine but Newark to Nashville was too long

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

Excellent communication from the staff. We actually arrived early. Very friendly and professional staff.

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.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

Boarding was awful - no order, people cutting in line, completely chaotic Planes are very old and uncomfortable. Noticeable difference between Delta and United on same route.

Getting to Scotland with no luggage (no medicine, no clothes and no club) on golf trip very disappointed

My luggage never made it, I booked business class only to find out I’m sitting in the back. Very disappointed with the reservation

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