HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$238+ Cheap flights from Key West to Portland (EYW - PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Key West to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 16, 2025.

Round-trip from

$314
(American Airlines)

One-way from

$238
(Delta)

Popular in

August

Cheapest in

September

Average price

$488
From Key West to Portland
Search Deals
One-way flight from Key West to Portland
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Key West to Portland

Cheapest flights from Key West to Portland
Explore the most affordable flight options available from Key West to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2025.

This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1612:00 pmEYW - PDX
1 stop11h 28mAmerican Airlines
Sun 9/215:38 amPDX - EYW
2 stops10h 21mAmerican Airlines
Deal found 7/14$314
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:00 amEYW - PDX
2 stops11h 59mDelta
Thu 9/117:05 pmPDX - EYW
2 stops12h 50mDelta
Deal found 7/14$329

Cheapflights Fare Finder

Customize your flight search to find flights from Key West to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2025.
Use the filters below to find and compare flights from Key West to Portland that are best for you.

Fly from

Key West

Fly to

Portland

Route

Depart

Return

Price

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 9/16

12:00 pm-8:28 pm

1 stop11h 28m

Portland

Sun 9/21

5:38 am-6:59 pm

2 stops10h 21m

$314

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 9/4

7:00 am-3:59 pm

2 stops11h 59m

Portland

Thu 9/11

7:05 pm-10:55 am

2 stops12h 50m

$329

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 10/3

2:00 pm-9:47 pm

1 stop10h 47m

$238

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

4:00 pm-10:35 pm

1 stop9h 35m

$288

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

12:12 pm-11:07 pm

1 stop13h 55m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

Best time to book a flight from Key West to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Key West with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Key West to Portland

What is the cheapest time of day to fly from EYW to PDX?

Find hourly flight availability from Key West to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Key West to Portland at noon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated July 16, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Key West to Portland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
United Airlines
7.4
Good
8,863 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Key West to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Key West to Portland round-trip?

    Cheapflights users have booked flights from Key West to Portland round-trip from $314. Another airline that can offer you cheap pricing is Delta. American Airlines is 39% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Key West to Portland one-way?

    One-way options have recently been found by users for as low as $238 on Delta. Other airlines that offer cheap prices include United Airlines from $288 and American Airlines from $314 one-way.

  • Can I find deals for flights from Key West to Portland that include hotel bookings?

    Yes. In addition to deals on Key West to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Portland.

  • Can I find deals for business class flights from Key West to Portland?

    Yes. Cheapflights offers flight deals from Key West to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Key West to Portland?

    Currently, November is the cheapest month in which you can book a flight from Key West to Portland (average of $277). Flying from Key West to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Seaside
Vancouver
Beaverton
Clackamas
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Astoria
Long Beach
Cannon Beach
Tigard
Longview
Hood River
Depoe Bay
Woodburn
Stevenson
Wilsonville
Pacific City
Troutdale

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to Portland flights
Jacksonville to Boise flights
Tampa to Portland flights
Fort Lauderdale to Portland flights
Miami to Portland flights
Jacksonville to Portland flights
Orlando to Boise flights
West Palm Beach to Portland flights
Gainesville to Boise flights
Tampa to Boise flights
Fort Myers to Portland flights
Valparaiso to Portland flights
Miami to Boise flights
Tampa to Medford flights
Jacksonville to Redmond flights
Sarasota to Portland flights
Tampa to Eugene flights
Pensacola to Portland flights
Orlando to Eugene flights
Fort Lauderdale to Eugene flights
Melbourne to Portland flights
Jacksonville to Eugene flights
Fort Lauderdale to Redmond flights
Tampa to Redmond flights
Jacksonville to Medford flights
Daytona Beach to Portland flights
Tallahassee to Portland flights
Orlando to Redmond flights
Orlando to Medford flights
Panama City to Portland flights
Miami to Eugene flights
West Palm Beach to Eugene flights
Fort Lauderdale to Medford flights
Miami to Redmond flights
Fort Myers to Boise flights
Pensacola to Eugene flights
Pensacola to Medford flights
Gainesville to Portland flights
Valparaiso to Boise flights
West Palm Beach to Boise flights
Sarasota to Redmond flights
Fort Lauderdale to Boise flights
Fort Myers to Eugene flights
West Palm Beach to Redmond flights
Pensacola to Boise flights
Fort Myers to Medford flights
Gainesville to Eugene flights
West Palm Beach to Medford flights
Sarasota to Boise flights

Top 2 airlines flying from Key West to Portland

Discover the top 2 airlines that operate flights from Key West to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$574FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.