EYW - PDX

$389 Find Cheap Flights from Key West to Portland

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Portland departing on 4/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Portland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Portland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Portland, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$343
Multiple Airlines
Thu 4/30Thu 5/28
EYW - PDX • 2 stops
Top airlines
Delta
Cheapest • from $389 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Key West and Portland. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Dallas (DFW)
Cheapest • Avg $388 (round-trip)
Dallas (DFW)
Shortest trip • 10h 07m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Key West to Portland (EYW-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Portland

Thu, Apr 30 - Thu, May 28
Multiple Airlines Logo
9:58 am - 11:42 am
EYW
-
PDX
52h 44m
2 stops
Multiple Airlines Logo
2:44 pm - 11:02 am
PDX
-
EYW
17h 18m
1 stop
$343Multiple Airlines
Wed, Sep 2 - Mon, Sep 14
Delta Logo
7:00 am - 1:06 pm
EYW
-
PDX
9h 06m
1 stop
Delta Logo
9:45 pm - 10:58 am
PDX
-
EYW
10h 13m
1 stop
$389Delta
Thu, May 14 - Sat, May 23
Delta Logo
11:48 am - 10:02 pm
EYW
-
PDX
13h 14m
2 stops
Delta Logo
9:39 pm - 10:53 am
PDX
-
EYW
10h 14m
1 stop
$394Delta
Thu, May 14 - Sat, May 23
Delta Logo
11:48 am - 10:02 pm
EYW
-
PDX
13h 14m
2 stops
Delta Logo
11:12 pm - 5:23 pm
PDX
-
EYW
15h 11m
2 stops
$399Delta
Thu, May 14 - Sat, May 23
American Airlines Logo
2:29 pm - 10:50 pm
EYW
-
PDX
11h 21m
1 stop
American Airlines Logo
10:59 pm - 1:41 pm
PDX
-
EYW
11h 42m
2 stops
$414American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 10:50 pm
EYW
-
PDX
9h 52m
2 stops
American Airlines Logo
10:59 pm - 4:07 pm
PDX
-
EYW
14h 08m
2 stops
$419American Airlines
Wed, Sep 2 - Wed, Sep 16
American Airlines Logo
11:26 am - 8:52 pm
EYW
-
PDX
12h 26m
2 stops
American Airlines Logo
5:20 am - 6:27 pm
PDX
-
EYW
10h 07m
2 stops
$420American Airlines
Thu, May 14 - Sat, May 23
Delta Logo
7:30 am - 12:54 pm
EYW
-
PDX
8h 24m
1 stop
Delta Logo
9:39 pm - 10:53 am
PDX
-
EYW
10h 14m
1 stop
$452Delta
Thu, Sep 3 - Tue, Sep 15
Delta Logo
7:00 am - 1:06 pm
EYW
-
PDX
9h 06m
1 stop
Delta Logo
5:10 pm - 10:58 am
PDX
-
EYW
14h 48m
2 stops
$457Delta
Wed, Sep 2 - Wed, Sep 16
Delta Logo
7:00 am - 4:10 pm
EYW
-
PDX
12h 10m
2 stops
Delta Logo
5:30 am - 7:45 pm
PDX
-
EYW
11h 15m
2 stops
$462Delta
Booking Insights

KAYAK's insights & trends for Key West to Portland flights

Get data-powered insights and trends into flights from Key West to Portland to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Key West to Portland?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Portland were found on Delta ($389) and American Airlines ($414).

Find deals

Good to know

Cheapest flight$343
Flight from Key West to Portland

When to book flights from Key West to Portland

Are your dates flexible? Find out the best times to travel from Key West to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Key West to Portland

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

    In the last 3 days, the lowest price for a flight from Key West to Portland was $343 for a round-trip ticket.

  • Do I need a passport to fly between Key West and Portland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Key West to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Key West to Portland?

    oneworld is the only airline alliance operating flights between Key West and Portland.

  • How does KAYAK find such low prices on flights from Key West to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Key West is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Key West with another airline. Booking your flights between Key West and PDX can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Key West to Portland

 
See real verified KAYAK customer reviews for airlines flying from Key West to Portland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11520 reviews
6.9Entertainment
7.2Comfort
7.9Crew
6.4Food
7.5Boarding
Airline reviews

The flight attendant in business class was excellent! Professional, friendly and attentive.

10.0 ExcellentTy, Mar 2026
MIA - DFW
Read more American Airlines reviews

The flight attendant in business class was excellent! Professional, friendly and attentive.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

It was great. Smooth flight, comfortable, left on time and landed on time.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

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

Information on your arrival and departure airports

Key West (EYW)
Portland (PDX)