$142 Cheap flights to Portland

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Top places to visit in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.
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Port Antonio

Port Antonio

Cheap flights to Portland from $142 One Way, $315 Round Trip

$315 return flights and $142 one-way flights to Portland were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 12 - Thu, Oct 8
YYZ
Toronto
KIN
Kingston
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Select Arajet flight, departing Sat, Sep 12 from Toronto to Kingston, returning Thu, Oct 8, priced at $315 found 6 days ago
Tue, Dec 8 - Wed, Dec 23
LGA
New York
KIN
Kingston
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Dec 8 from New York to Kingston, returning Wed, Dec 23, priced at $367 found 2 days ago
Tue, Dec 1 - Fri, Dec 4
JFK
New York
KIN
Kingston
$367 Roundtrip, found 18 hours ago
$367
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Dec 1 from New York to Kingston, returning Fri, Dec 4, priced at $367 found 18 hours ago
Fri, Sep 25 - Fri, Oct 2
FLL
Fort Lauderdale
KIN
Kingston
$419 Roundtrip, found 1 hour ago
$419
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Sep 25 from Fort Lauderdale to Kingston, returning Fri, Oct 2, priced at $419 found 1 hour ago
Sat, Oct 17 - Sat, Oct 24
MIA
Miami
KIN
Kingston
$423 Roundtrip, found 1 day ago
$423
Roundtrip
found 1 day ago
Select Arajet flight, departing Sat, Oct 17 from Miami to Kingston, returning Sat, Oct 24, priced at $423 found 1 day ago
Sat, Oct 3 - Tue, Oct 6
EWR
New York
KIN
Kingston
$424 Roundtrip, found 1 day ago
$424
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 3 from New York to Kingston, returning Tue, Oct 6, priced at $424 found 1 day ago
Thu, Sep 17 - Sun, Sep 20
BOS
Boston
KIN
Kingston
$465 Roundtrip, found 3 days ago
$465
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 17 from Boston to Kingston, returning Sun, Sep 20, priced at $465 found 3 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YYZKingstonAugust 8 to September 21$503
LGAKingstonAugust 9 to August 22$561
JFKKingstonAugust 7 to August 15$576
FLLKingstonAugust 9 to August 30$586
MIAKingstonAugust 8 to August 12$609
ATLKingstonAugust 9 to August 25$609
BOSKingstonAugust 7 to August 30$743
MCOKingstonAugust 9 to August 16$862
NASKingstonAugust 7 to August 14$865
POSKingstonAugust 9 to August 14$1,059
JFKBoscobelAugust 7 to August 12$1,249
JFKBoscobelAugust 7 to August 12$1,249
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Portland Accommodation Deals

Hotel Tim Bamboo

Hotel Tim Bamboo

3 out of 5
5 Eveleigh Park Road Port Antonio Portland
$130 nightly
The price is $144 total per night from Sep 2 to Sep 3
$144 total
Sep 2 - Sep 3
Total with taxes and fees
Stay at this hotel in Port Antonio. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowHotel Tim Bamboo
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.

Our Top Portland Apartment Hotels

Bonne Amie

Bonne Amie

3.5 out of 5
San San, Blue Lagoon Port Antonio Portland
Stay at this villa in Port Antonio. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Blue Lagoon and San San Beach are ...
Get rates
Opens in a new windowBonne Amie
Amazing Caribbean Sea & Mountain Views, Luxury, Privacy, 4 bd suites, sleeps 12

Amazing Caribbean Sea & Mountain Views, Luxury, Privacy, 4 bd suites, sleeps 12

San San Port Antonio
Book a stay at this family-friendly vacation home in Port Antonio. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Blue Lagoon and ...
Get rates
Opens in a new windowAmazing Caribbean Sea & Mountain Views, Luxury, Privacy, 4 bd suites, sleeps 12
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
$115 nightly
The price is $134 total per night from Sep 2 to Sep 3
$134 total
Sep 2 - Sep 3
Total with taxes and fees
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 ...
9.2/10 Wonderful! (230 reviews)
"More Than a Hotel—A True Jamaican Experience Great Huts is not just a hotel—it is an experience. The property stretches from the cliffs down to the beach, with winding paths through sea grape trees, coral rock, African-inspired art, treehouses, hidden sitting areas, and incredible views of the Caribbean. ..."

Reviewed on Aug 1, 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.

Score Epic Portland Accommodation Deals

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
$121 nightly
The price is $133 total per night from Sep 2 to Sep 3
$133 total
Sep 2 - Sep 3
Total with taxes and fees
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 ...
8/10 Very Good! (220 reviews)
"WiFi wasn’t working at first but besides that no complaints"

Reviewed on Aug 2, 2026

Opens in a new windowSea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $184 total per night from Aug 11 to Aug 12
$184 total
Aug 11 - Aug 12
Total with taxes and fees
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 ...
8.2/10 Very Good! (344 reviews)
"."

Reviewed on Aug 2, 2026

Opens in a new windowJamaica Palace Hotel
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
$115 nightly
The price is $134 total per night from Sep 2 to Sep 3
$134 total
Sep 2 - Sep 3
Total with taxes and fees
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 ...
9.2/10 Wonderful! (230 reviews)
"More Than a Hotel—A True Jamaican Experience Great Huts is not just a hotel—it is an experience. The property stretches from the cliffs down to the beach, with winding paths through sea grape trees, coral rock, African-inspired art, treehouses, hidden sitting areas, and incredible views of the Caribbean. ..."

Reviewed on Aug 1, 2026

Opens in a new windowGreat Huts
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LF Jungle Retreat

LF Jungle Retreat

3 out of 5
Lots 32-40, Willamsfield Port Antonio
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Aug 6 to Aug 7
$103 total
Aug 6 - Aug 7
Total with taxes and fees
Stay at this hotel in Port Antonio. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Blue Lagoon and Trident Castle are located ...
8.4/10 Very Good! (64 reviews)
"We had a great stay, staff was amazing it was so peaceful! I would definitely come back !"

Reviewed on Jul 28, 2026

Opens in a new windowLF Jungle Retreat
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.

Family Friendly Hotels in Portland

San San Tropez
Great for families

San San Tropez

3 out of 5
San San Port Antonio Portland
Book a stay at this family-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and private pools. Popular attractions Blue Lagoon and Frenchman's ...
7.4/10 Good! (30 reviews)

Families like: Private pool, playground, babysitting, close to beach

Requires updating
"Great location. Rooms are clean but very dated property with poor facilities. Needs urgent renovation Friendly and approachable staff."

Reviewed on Jan 15, 2019

Get rates
Opens in a new windowSan San Tropez
All Nations Guesthouse
Great for families

All Nations Guesthouse

3 out of 5
Skipper Blvd, San San Port Antonio
$85 nightly
The price is $99 total per night from Aug 5 to Aug 6
$99 total
Aug 5 - Aug 6
Total with taxes and fees
Book a stay at this family-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and private pools. Popular attractions Blue Lagoon and Frenchman's ...
8.8/10 Excellent! (151 reviews)

Families like: Private pool, kitchen, playground, close to beach

Travelers say...
"The nicest staff I’ve met! I had a car problem and they all were extremely supportive and sweet. I will definitely be coming back. Super grateful for them!"

Reviewed on Jul 31, 2026

Opens in a new windowAll Nations Guesthouse
Bay View Eco Resort & Spa

Bay View Eco Resort & Spa

3 out of 5
Anchovy Port Antonio Portland
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $180 total per night from Aug 4 to Aug 5
$180 total
Aug 4 - Aug 5
Total with taxes and fees
Book a stay at this spa resort in Port Antonio. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Blue Lagoon and Trident Castle are ...
7.8/10 Good! (102 reviews)
"N/a"

Reviewed on Jul 20, 2026

Opens in a new windowBay View Eco Resort & Spa
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Bonne Amie

Bonne Amie

3.5 out of 5
San San, Blue Lagoon Port Antonio Portland
Stay at this villa in Port Antonio. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Blue Lagoon and San San Beach are ...
Get rates
Opens in a new windowBonne Amie
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Portland

If you are looking for discount prices on flights to Portland then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Portland flights easy and affordable.

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Orbitz makes it stress-free to book Portland flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Portland, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your Portland flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

Frequently asked questions

How much is a flight to Portland?
Round-trip fares dropped as low as $315 this past week to Portland, and rose to a high of $1,249. A few lucky passengers flying out of New York (LGA) managed to score one-way fares starting from just $142.
How to book the cheapest flight to Portland?
With some of the most amazing flight deals around, you'll always jet for less with Orbitz. The following tips and hints will help you snap up cheap flights to Portland — and leave you with extra cash in your wallet:

  • Departing from or arriving at nearby airports may work out to be cheaper. Type in your preferred departure and arrival airports. Next, select the 'Nearby airports' function below the form fields to explore your options.
  • Also, click on the 'Show flexible dates' option to see the airfares on days around your selected departure. You may be able to score cheaper flight deals if your travel dates are flexible.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • Reserve your seat as soon as you've decided on your travel dates. While you can get lucky now and then, airline tickets rarely get more affordable as your departure date nears.
  • Make serious savings on your trip by bundling your hotel, flights and car rentals into an Orbitz package deal. Your bank account will thank you for it.
  • Flying during busier seasons often means steep airfares. Try to plan your vacation outside of popular dates, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Portland?
Reserve your seats to Portland in January. This is the best time of the year for bargain airfares, closely followed by February and August. Pick up cheap flights and enjoy your dream getaway with Orbitz.
What day of the week is the cheapest to book a flight to Portland?
When it comes to cheap fares to Portland, the best days to book are generally Tuesdays, Wednesdays and Saturdays. An unbeatable flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Portland?
Everybody enjoys a bargain, so we suggest leaving earlier in the week for cheap flights to Portland. Orbitz data from 2020 shows you can pick up the best deals on flights that depart on Mondays. Tuesday is the next most affordable day, while Saturdays are likely to cost an arm and a leg. Many passengers like to travel at the weekend, so leave those Saturdays for catching up with friends.
What is the cheapest month to fly to Portland?
To score cheap flights to Portland, pack your suitcase and jet off in August. Orbitz data has found that generally, this is the best month to save on your fare. If you want to jet to Portland during June, it's worth keeping in mind that this is the most expensive time of year to travel.
Which airlines allow free cancellation?
Orbitz makes it a piece of cake to find carriers offering fare flexibility. Simply choose "Filter by flexible change policies" when searching for your flights and bingo! We'll show you options that include free cancellation, no change fees and of course, an amazing low price.
What do I need for the flight to Portland?
There is so much to plan for any big trip, so it's nice to get a bit of help before you set out. Here are a few suggestions to ensure that you're prepared for departure:

  • You'll need to take all relevant travel documents and some identification. How much is dependent on your place of departure. At the time of booking, you should always use the same name, birth date and gender as stated on your current ID.
  • Stuff your carry-on bag with activities and snacks and watch time whiz by on this medium-haul flight. If you can, join the airport's Wi-Fi and transfer your favorite playlist or podcast to your phone or tablet prior to take off.
  • Airplane cabins can often get quite cool. Even if you're traveling during the peak of the Portland summer, make sure you take an extra warm layer to keep comfortable.

How many direct flights are there to Portland?
Every month, there are 42 direct flights into Portland. Take your pick of a wide range of airline companies, including JetBlue Airways, American Airlines and Caribbean Airlines. Other popular carriers that jet to Portland nonstop are interCaribbean Airways, Cayman Airways and Spirit Airlines.
How do I get cheap first-class/business deals to Portland?
If you think a first or business-class ticket is way out of your reach, you may want to think again. Here are some practical tips to help you pick up a premium flight to Portland for a whole lot less:

  • Flexibility is essential. By being open to a variety of travel dates, you'll have more chances of landing a great deal on your airfares.
  • A lot of budget airlines these days have excellent business or premium-class seating for a reasonable price.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat up the front. You may also be able to upgrade with points earned through a loyalty program.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.