$132 Cheap flights to Portland

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Top places to visit in Portland

Cheap flights to Portland from $132 One Way, $356 Round Trip

$356 return flights and $132 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.

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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCOKingstonJune 21 to June 30$444
YYZKingstonJune 19 to June 24$460
MIAKingstonJune 19 to June 24$484
FLLKingstonJune 21 to June 28$487
EWRKingstonJune 21 to June 27$518
JFKKingstonJune 20 to July 8$528
BOSKingstonJune 20 to June 25$569
ATLKingstonJune 19 to June 22$653
NASKingstonJune 19 to June 26$705
JFKBoscobelJune 19 to June 23$1,173
JFKBoscobelJune 19 to June 23$1,173
FLLBoscobelJune 19 to June 21$3,368
*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
$120 nightly
The price is $133 total per night from Jun 18 to Jun 19
$133 total
Jun 18 - Jun 19
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 ...
7.2/10 Good! (201 reviews)
"Staff was wonderful, food was great."

Reviewed on May 17, 2026

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 Frenchman's Cove Beach ...
Opens in a new windowBonne Amie
Luxury Privacy, Beach and Mountain View’s. 4 bedroom suites, sleeps 12..

Luxury Privacy, Beach and Mountain View’s. 4 bedroom 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 ...
Opens in a new windowLuxury Privacy, Beach and Mountain View’s. 4 bedroom suites, sleeps 12..
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
$131 nightly
The price is $152 total per night from Jun 18 to Jun 19
$152 total
Jun 18 - Jun 19
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! (223 reviews)
"Unfortunately there was a power outage when we arrived. Tanya was fantastic and made sure to find alternative suitable accommodation for us. I would recommend the hotel for location and price and staff friendliness and would return in the future"

Reviewed on Jun 9, 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
$136 nightly
The price is $149 total per night from Jul 1 to Jul 2
$149 total
Jul 1 - Jul 2
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! (209 reviews)
"The food was great Did encounter a very rude staff other than HER ..!!! the staff was great Maintaining the property very poorly I could write a two page paragraph on this, but I will just say do better the view was awesome. I loved it. Breakfast was great.house keeping was great.🙏"

Reviewed on Jun 16, 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
$184 nightly
The price is $204 total per night from Jun 18 to Jun 19
$204 total
Jun 18 - Jun 19
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! (309 reviews)
"This place was amazing!!"

Reviewed on Jun 16, 2026

Opens in a new windowJamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
$377 nightly
The price is $418 total per night from Jun 28 to Jun 29
$418 total
Jun 28 - Jun 29
Total with taxes and fees
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. ...
Opens in a new windowGeejam
Save an average of 15% on thousands of hotels when you're signed in
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
$131 nightly
The price is $152 total per night from Jun 18 to Jun 19
$152 total
Jun 18 - Jun 19
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! (223 reviews)
"Unfortunately there was a power outage when we arrived. Tanya was fantastic and made sure to find alternative suitable accommodation for us. I would recommend the hotel for location and price and staff friendliness and would return in the future"

Reviewed on Jun 9, 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.

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 Frenchman's Cove Beach ...
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

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 Jun 22 to Jun 23
$99 total
Jun 22 - Jun 23
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 Frenchman's Cove Beach ...
8.8/10 Excellent! (148 reviews)

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

Travelers say...
"We really enjoyed our stay at All Nations Guesthouse. The staff was fantastic and very accommodating. The views from the property are amazing…seeing the Caribbean over the tops of the trees was special! Having the communal kitchen was very welcoming. We certainly recommend a stay at the ..."

Reviewed on Jun 15, 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 Jun 18 to Jun 19
$180 total
Jun 18 - Jun 19
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 Frenchman's Cove Beach and Blue Lagoon ...
7.8/10 Good! (100 reviews)
"Everything was perfect 👌"

Reviewed on May 12, 2026

Opens in a new windowBay View Eco Resort & Spa
Save an average of 15% on thousands of hotels when you're signed in
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 Frenchman's Cove Beach ...
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?

Portland

Snag some “suite” deals when you add cheap hotel rooms to Portland flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Portland.

Fun for All

While shopping Orbitz sales on Portland flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Portland flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Portland. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

Frequently asked questions

How much is a flight to Portland?
Round-trip fares dropped as low as $356 this past week to Portland, and rose to a high of $3,368. A few lucky passengers flying out of New York (EWR) managed to score one-way fares starting from just $132.
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.