How long is the flight from Key West to Portland?

Departing from Key West to Portland will take you 10h 24m. Airlines will cover a distance of 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What is the cheapest airline to fly from Key West to Portland round-trip?

Cheapflights users have booked flights from Key West to Portland round-trip from $344.

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.

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).

Most accurate provider : When it comes to deals on Key West-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Portland flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Key West-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$234+ Flights from Key West to Portland

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1. Tell us where you want to go

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Cheap 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 dezembro 5, 2025.

sáb 12/62:36 pmEYW - PDX

1 stop9h 31mAmerican Airlines

sáb 12/610:45 pmPDX - EYW

1 stop9h 17mAmerican Airlines

Deal found 12/3

$855

sáb 12/67:40 amEYW - PDX

2 stops13h 03mDelta

sáb 12/611:20 pmPDX - EYW

2 stops11h 47mDelta

Deal found 12/3

$871

Best flights from Key West to Portland
Discover carefully curated flight deals from Key West to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated dezembro 5, 2025.

qua 1/142:25 pmEYW - PDX

1 stop10h 24mUnited Airlines

dom 1/1811:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Deal found 12/2

$359

qui 5/143:55 pmEYW - PDX

1 stop7h 59mAmerican Airlines

sáb 5/2310:40 pmPDX - EYW

1 stop9h 34mAmerican Airlines

Deal found 12/4

$359

qui 5/142:35 pmEYW - PDX

1 stop10h 50mDelta

sáb 5/239:45 pmPDX - EYW

1 stop10h 13mDelta

Deal found 12/3

$384

qui 5/284:05 pmEYW - PDX

1 stop9h 03mUnited Airlines

qui 6/411:07 amPDX - EYW

1 stop8h 04mUnited Airlines

Deal found 12/2

$392

qui 5/283:02 pmEYW - PDX

1 stop8h 26mAmerican Airlines

qui 6/411:52 pmPDX - EYW

2 stops12h 30mAmerican Airlines

Deal found 12/2

$471

qua 1/214:15 pmEYW - PDX

2 stops24h 30mUnited Airlines

dom 1/2511:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Deal found 12/4

$453

Last-minute flights from Key West to Portland
Discover last-minute flight deals from Key West to Portland. Data last updated dezembro 5, 2025 and is based on user searches.

sáb 12/62:36 pmEYW - PDX

1 stop9h 31mAmerican Airlines

sáb 12/610:45 pmPDX - EYW

1 stop9h 17mAmerican Airlines

Deal found 12/3

$855

sáb 12/67:40 amEYW - PDX

2 stops13h 03mDelta

sáb 12/611:20 pmPDX - EYW

2 stops11h 47mDelta

Deal found 12/3

$871

qua 1/142:25 pmEYW - PDX

1 stop10h 24mUnited Airlines

dom 1/1811:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Deal found 12/2

$359

qua 1/214:15 pmEYW - PDX

2 stops24h 30mUnited Airlines

dom 1/2511:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Deal found 12/4

$453

One-way flights from Key West to Portland
Search for one-way flight options from Key West to Portland. Find affordable one-way fares based on user searches. Data last updated dezembro 5, 2025.

ter 12/1611:45 amEYW - PDX

3 stops50h 52mMultiple Airlines

Deal found 12/2

$234

sex 12/128:55 amEYW - PDX

3 stops26h 58mMultiple Airlines

Deal found 12/3

$252

sex 2/273:35 pmEYW - PDX

3 stops53h 31mMultiple Airlines

Deal found 12/4

$257

qua 12/1010:47 amEYW - PDX

3 stops32h 50mMultiple Airlines

Deal found 12/3

$274

sex 2/274:02 pmEYW - PDX

1 stop10h 57mAmerican Airlines

Deal found 12/4

$343

qua 12/102:39 pmEYW - PDX

1 stop9h 45mAmerican Airlines

Deal found 12/3

$431

qua 12/314:29 pmEYW - PDX

1 stop9h 30mUnited Airlines

Deal found 12/4

$439

sex 12/124:05 pmEYW - PDX

1 stop9h 10mUnited Airlines

Deal found 12/3

$485

Find flight deals from Key West to Portland

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 1 star
Round-trip from	$359 (United Airlines)
One-way from	$234 (Kiwi.com)

Provider with most accurate pricing for Key West-Portland flight deals.

Search Deals

Provider most trusted by Cheapflights users for Key West-Portland flights.

Search Deals

From Key West to Portland

Search Deals

One-way flight from Key West to Portland

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Key WestPortland

EYW - PDX

EYWPDX

Key West

qua 1/14

2:25 pm-9:49 pm

1 stop10h 24m

Portland

dom 1/18

11:05 pm-1:03 pm

1 stop10h 58m

$359

Key WestPortland

EYW - PDX

EYWPDX

Key West

qui 5/14

3:55 pm-8:54 pm

1 stop7h 59m

Portland

sáb 5/23

10:40 pm-11:14 am

1 stop9h 34m

$359

Key WestPortland

EYW - PDX

EYWPDX

Key West

qui 5/14

2:35 pm-10:25 pm

1 stop10h 50m

Portland

sáb 5/23

9:45 pm-10:58 am

1 stop10h 13m

$384

Key WestPortland

EYW - PDX

EYWPDX

Key West

qui 5/28

4:05 pm-10:08 pm

1 stop9h 03m

Portland

qui 6/4

11:07 am-10:11 pm

1 stop8h 04m

$392

Key WestPortland

EYW - PDX

EYWPDX

Key West

qua 1/21

4:15 pm-1:45 pm

2 stops24h 30m

Portland

dom 1/25

11:05 pm-1:03 pm

1 stop10h 58m

$453

Key WestPortland

EYW - PDX

EYWPDX

Key West

qui 5/28

3:02 pm-8:28 pm

1 stop8h 26m

Portland

qui 6/4

11:52 pm-3:22 pm

2 stops12h 30m

$471

Key WestPortland

EYW - PDX

EYWPDX

Key West

ter 12/16

11:45 am-11:37 am

3 stops50h 52m

$234

Key WestPortland

EYW - PDX

EYWPDX

Key West

sex 12/12

8:55 am-8:53 am

3 stops26h 58m

$252

Key WestPortland

EYW - PDX

EYWPDX

Key West

sex 2/27

3:35 pm-6:06 pm

3 stops53h 31m

$257

Key WestPortland

EYW - PDX

EYWPDX

Key West

qua 12/10

10:47 am-4:37 pm

3 stops32h 50m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 14 results

Most accurate provider: When it comes to deals on Key West-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Portland flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Key West-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

A simple way to save on the total cost of your ticket is to fly from Key West to Portland in the evening. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Portland

Read reviews from past customers who have flown 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.

American Airlines

7.2

Good

11,047 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

American Airlines

7.2

Good

11,047 reviews

American Airlines

7.2

Good

11,047 reviews

Reviews

1 / 20

2.0

Mediocre

Anonymous,Aug 2025

MIA - DCA

Related info for your journey

How long is the flight from Key West to Portland?
Departing from Key West to Portland will take you 10h 24m. Airlines will cover a distance of 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.
What is the cheapest airline to fly from Key West to Portland round-trip?
Cheapflights users have booked flights from Key West to Portland round-trip from $344.
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.

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Complete your trip

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Other flights to Portland

Top airline flying from Key West to Portland

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$344	Average$574	FlexibilityNo cancel fee	On-time71%

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$234+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Key West to Portland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Key West to Portland

Cheapest flights from Key West to PortlandExplore 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 dezembro 5, 2025.

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 dezembro 5, 2025.

Find flight deals from Key West to Portland

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Cheapflights Fare Finder

Use the filters below to find and compare flights from Key West to Portland that are best for you.

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.

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?

Reviews of airlines servicing Portland

Read reviews from past customers who have flown 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.

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.

How long is the flight from Key West to Portland?

What is the cheapest airline to fly from Key West to Portland round-trip?

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

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

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

Traveling to a place near Portland?

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.

Top airline flying from Key West to Portland

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Book with Flexibility

Travel Smart

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 dezembro 5, 2025.