Cheap Flights to Portland (2026/2027)

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Port Antonio

Flights
Port Antonio
OriginDestinationTravel DatesFlights From*
YYZKingstonAugust 24 to August 31$340
JFKKingstonAugust 25 to September 8$395
JFKKingstonAugust 25 to September 8$395
BOSKingstonJune 14 to June 18$416
MIAKingstonAugust 1 to September 30$425
MCOKingstonJuly 29 to August 2$444
ATLKingstonAugust 16 to August 23$446
FLLKingstonJune 30 to July 4$469
MIABoscobelJuly 19 to July 23$554
ATLBoscobelAugust 19 to August 26$628
POSKingstonJuly 17 to July 24$671
MCOBoscobelJune 29 to July 5$709
LGABoscobelJuly 14 to July 18$714
NASKingstonJune 19 to June 22$715
BOSBoscobelJune 19 to June 23$854
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YYZKingstonMay 30 to June 1$442
BOSKingstonMay 30 to August 30$455
MIAKingstonMay 30 to June 7$459
FLLKingstonMay 31 to June 10$486
LGAKingstonMay 30 to June 7$499
JFKKingstonMay 31 to June 4$517
MCOKingstonMay 31 to June 2$672
ATLKingstonMay 31 to June 6$780
*Prices include taxes and fees

Best Portland Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa
3.0-star property

Blue Berry Hills Villa

Jun 18 - Jun 23

5 night stay

Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

Copa • Non-stop roundtrip • Coach
Price was $2,835, price is now $2,384 per person
$2,384
per person
found 5 hours ago
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Portland
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Travelers ❤️ These Portland 🏨

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Stay at this hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located nearby.
8.2/10 Very Good! (201 reviews)
"Sea cliff's property was beautiful and my partner and I have an amazing time on the quiet property. The rooms were clean and the housekeeping came every morning. We do wish the air conditioner was more efficient and cooled the entire room, it only cooled one side. The lunch/dinner was great, it was ..."

Reviewed on May 26, 2026

Opens in a new windowSea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Book a stay at this business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Trident Castle and Frenchman's Cove Beach are located nearby.
8.4/10 Very Good! (303 reviews)
"I have stay here before and was very happy they could accommodate my family and I.. We booked another accommodation which was not as advertised… Breakfast is on point and with a wide choice. Room was clean and smells clean too… Great location to pop into town or to Boston beach… I will be back.."

Reviewed on May 19, 2026

Opens in a new windowJamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
Book a stay at this luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Frenchman's Cove Beach and San San Beach are located nearby.
9.6/10 Exceptional! (90 reviews)
"Property and scenery was great . Awesome staff. Room and bathroom well decorated with pictures of music musicians in black and white also country folks. Food was delicious also property , pools and surroundings is well kept ."

Reviewed on May 14, 2026

Opens in a new windowGeejam
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Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
Book a stay at this beach resort in Port Antonio. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Boston Bay Beach and Winnifred Beach are located nearby.
9.2/10 Wonderful! (222 reviews)
"My family and I spent one night over our 4 day adventure in Portland. Our first time experiencing an eco-tourism type of accommodation. It was amazing. We stayed in the Fig Tree hut and all I can say is it is the best room of the house. They are undergoing some renovation but no disruption to our ..."

Reviewed on May 21, 2026

Opens in a new windowGreat Huts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Portland?
In the last seven days, the cheapest roundtrip flight to Portland cost $340 on this site. Take a look at our fantastic deals, make a booking and look forward to your next travel adventure. This price was available on Travelocity for flights to Portland departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Portland?
August is the cheapest month to fly to Portland based on Travelocity's direct return flight demand between January and December last year. We can help you snap up a great bargain so you can start organizing your escape today.
How can I check my flight status to Portland?
Whether you'd like to check the status of your flight to Portland or change your itinerary, you'll find all the info you need on our customer portal, Trips. Click on "Trips" at the top of the Travelocity homepage, then log in or create a new account. Another helpful way to view and manage all your bookings is with the Travelocity app. Get alerts about gate changes or flight delays and share updates with any friends or family flying with you.
How do I find the best deals on flights to Portland?
Be flexible with your dates and you might just find an incredible deal. When searching for flights on Travelocity, select the "Flexible dates" box at the top of the page to see all the prices for surrounding days. Also try to book early and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Portland was $340. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Portland with Travelocity?
A memorable vacation is at the click of a button when you book your trip with Travelocity. With great deals on cheap family flights, accommodations and more, we make it simple to find awesome prices to suit your needs. You can also make use of our 24/7 online chat support and free cancellations on most hotels during every stage of the process. Wander wisely with us and reserve your cheap flights to Portland today.
What are the most popular flight routes to Portland?
Browse through these busy flight routes to Portland and start planning your next great adventure:

  • New York, NY (JFK-John F. Kennedy Intl.) to Norman Manley Intl. Airport (KIN) - 749 flights a month.
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to Norman Manley Intl. Airport (KIN) - 706 flights a month.
  • Providenciales (PLS-Providenciales Intl.) to Norman Manley Intl. Airport (KIN) - 212 flights a month.

How much is a flight to Portland on average?
Airfares for roundtrip flights to Portland cost between $340 and $854 in the last seven days. The moment you see a terrific deal, lock it in and get ready to take off on your next fun adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Portland?
The length of your direct flight to Portland mostly depends on your starting point. For a good idea of what to expect, here are the average travel times for a handful of in-demand routes to Portland:

  • New York, NY (JFK-John F. Kennedy Intl.) to Norman Manley Intl. Airport (KIN) - 3 hours and 50 minutes
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to Norman Manley Intl. Airport (KIN) - 1 hour and 41 minutes
  • Providenciales (PLS-Providenciales Intl.) to Norman Manley Intl. Airport (KIN) - 1 hour and 20 minutes

What can I expect on a flight to Portland?
This depends on where you're leaving from and which air carrier you're flying with. You're likely to find all kinds of flights to Portland, from first class journeys to cheap flights for family vacations. For long-haul flights, airlines will typically offer entertainment and hot meals as well as games for the youngsters.