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$208+ 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
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$369
(United Airlines)

One-way from

$208
(United Airlines)

Popular in

August

Cheapest in

September

Average price

$563
From Key West to Portland
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One-way flight from Key West to Portland
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/82:45 pmEYW - PDX
2 stops29h 46mUnited Airlines
Sun 8/176:43 pmPDX - EYW
2 stops14h 32mUnited Airlines
Deal found 6/11$369
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 8/81:13 pmEYW - PDX
1 stop10h 03mAmerican Airlines
Sun 8/1711:07 pmPDX - EYW
1 stop11h 44mAmerican Airlines
Deal found 6/11$475
This Delta deal was found by Cheapflights users on 6/11. 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.
Fri 8/82:03 pmEYW - PDX
1 stop10h 46mDelta
Sat 8/1612:46 amPDX - EYW
2 stops13h 41mDelta
Deal found 6/11$592

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 June 12, 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

Fri 8/8

2:45 pm-5:31 pm

2 stops29h 46m

Portland

Sun 8/17

6:43 pm-12:15 pm

2 stops14h 32m

$369

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 8/8

1:13 pm-8:16 pm

1 stop10h 03m

Portland

Sun 8/17

11:07 pm-1:51 pm

1 stop11h 44m

$475

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 8/8

2:03 pm-9:49 pm

1 stop10h 46m

Portland

Sat 8/16

12:46 am-5:27 pm

2 stops13h 41m

$592

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 10/3

1:00 pm-6:31 pm

2 stops32h 31m

$208

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 10/3

7:00 am-1:26 pm

1 stop9h 26m

$289

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sat 10/4

12:00 pm-8:37 pm

1 stop11h 37m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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
7,950 reviews

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

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 $369. Other airlines that can offer you cheap pricing are American Airlines, from $475, and Delta, from $592. United Airlines is 28% 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 $208 on United Airlines. Other airlines that offer cheap prices include Delta from $289 and American Airlines from $316 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 Key West?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$548FlexibilityNo cancel feeOn-time71%

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