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$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. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$319
(Delta)

One-way from

$238
(Delta)

Popular in

August

Cheapest in

September

Average price

$420
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 July 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 julio 3, 2025.

This Delta deal was found by Cheapflights users on 7/3. 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.
mié. 9/242:00 pmEYW - PDX
2 stops12h 52mDelta
mar. 9/305:10 pmPDX - EYW
2 stops14h 45mDelta
Deal found 7/3$319
This American Airlines deal was found by Cheapflights users on 7/3. 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.
mié. 9/2412:00 pmEYW - PDX
1 stop11h 28mAmerican Airlines
mar. 9/309:56 pmPDX - EYW
1 stop10h 17mAmerican Airlines
Deal found 7/3$389
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/178:54 amEYW - PDX
2 stops25h 38mMultiple Airlines
dom. 7/2010:23 amPDX - EYW
3 stops27h 13mMultiple Airlines
Deal found 7/2$409
This United Airlines deal was found by Cheapflights users on 7/3. 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.
mié. 9/243:50 pmEYW - PDX
2 stops32h 16mUnited Airlines
mar. 9/305:30 amPDX - EYW
3 stops29h 49mUnited Airlines
Deal found 7/3$881

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 julio 3, 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

mié. 9/24

2:00 pm-11:52 pm

2 stops12h 52m

Portland

mar. 9/30

5:10 pm-10:55 am

2 stops14h 45m

$319

Key WestPortland

EYW - PDX

EYWPDX

Key West

mié. 9/24

12:00 pm-8:28 pm

1 stop11h 28m

Portland

mar. 9/30

9:56 pm-11:13 am

1 stop10h 17m

$389

Key WestPortland

EYW - PDX

EYWPDX

Key West

jue. 7/17

8:54 am-7:32 am

2 stops25h 38m

Portland

dom. 7/20

10:23 am-4:36 pm

3 stops27h 13m

$409

Key WestPortland

EYW - PDX

EYWPDX

Key West

mié. 9/24

3:50 pm-9:06 pm

2 stops32h 16m

Portland

mar. 9/30

5:30 am-2:19 pm

3 stops29h 49m

$881

Key WestPortland

EYW - PDX

EYWPDX

Key West

vie. 10/3

7:00 am-12:30 pm

1 stop8h 30m

$238

Key WestPortland

EYW - PDX

EYWPDX

Key West

sáb. 12/6

3:52 pm-8:58 pm

1 stop8h 06m

$283

Key WestPortland

EYW - PDX

EYWPDX

Key West

sáb. 12/6

3:00 pm-10:28 am

3 stops22h 28m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 julio 3, 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 julio 3, 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
7,982 reviews

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

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
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

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
7,982 reviews

Overall

8.0

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

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 $319. Other airlines that can offer you cheap pricing are American Airlines, from $389, and United Airlines, from $881. Delta is 38% 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 American Airlines from $283 and United Airlines from $425 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
Astoria
Long Beach
Cannon Beach
Tigard
Longview
Hood River
Depoe Bay
Woodburn
Stevenson
Pacific City
Troutdale
Gresham

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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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$548FlexibilityNo cancel feeOn-time71%

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