HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$207+ Cheap flights from Portland to Key West (PDX - EYW)

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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Key West 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.

Cheapflights Tip: The best prices from Portland to Key West are usually found in August or September, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Portland to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Key West (EYW). 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

$384
(United Airlines)

One-way from

$207
(United Airlines)

Popular in

June

Cheapest in

August

Average price

$781
From Portland to Key West
Search Deals
One-way flight from Portland to Key West
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Portland to Key West

Cheapest flights from Portland to Key West
Explore the most affordable flight options available from Portland to Key West. 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 6/10. 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.
Sun 8/176:43 pmPDX - EYW
2 stops14h 32mUnited Airlines
Fri 8/292:45 pmEYW - PDX
2 stops27h 40mUnited Airlines
Deal found 6/10$384
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 12/611:08 pmPDX - EYW
1 stop8h 59mAmerican Airlines
Wed 12/103:55 pmEYW - PDX
1 stop10h 21mAmerican Airlines
Deal found 6/9$389
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/278:22 amPDX - EYW
2 stops27h 46mMultiple Airlines
Tue 7/110:02 amEYW - PDX
2 stops34h 42mMultiple Airlines
Deal found 6/11$458
This Delta deal was found by Cheapflights users on 6/9. 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.
Tue 12/26:04 amPDX - EYW
1 stop8h 08mDelta
Fri 12/56:00 pmEYW - PDX
2 stops18h 04mDelta
Deal found 6/9$476
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/194:28 pmPDX - EYW
2 stops16h 02mAlaska Airlines
Sun 10/2612:11 pmEYW - PDX
2 stops24h 38mAlaska Airlines
Deal found 6/11$984

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Key West 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 Portland to Key West that are best for you.

Fly from

Portland

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 8/17

6:43 pm-12:15 pm

2 stops14h 32m

Key West

Fri 8/29

2:45 pm-3:25 pm

2 stops27h 40m

$384

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 12/6

11:08 pm-11:07 am

1 stop8h 59m

Key West

Wed 12/10

3:55 pm-11:16 pm

1 stop10h 21m

$389

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 6/27

8:22 am-3:08 pm

2 stops27h 46m

Key West

Tue 7/1

10:02 am-5:44 pm

2 stops34h 42m

$458

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 12/2

6:04 am-5:12 pm

1 stop8h 08m

Key West

Fri 12/5

6:00 pm-9:04 am

2 stops18h 04m

$476

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 10/19

4:28 pm-11:30 am

2 stops16h 02m

Key West

Sun 10/26

12:11 pm-9:49 am

2 stops24h 38m

$984

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/29

6:43 pm-6:05 pm

2 stops20h 22m

$207

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/29

9:30 pm-10:51 am

1 stop10h 21m

$258

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 7/28

12:59 am-4:12 pm

1 stop12h 13m

$547

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Best time to book a flight from Portland to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Portland 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 Portland to Key West

How far ahead should I book a flight from Portland to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Key West. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Key West, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland to Key West in March is currently the most expensive (average of $493). 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.

Rainfall in Key West by month

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

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

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

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Portland to Key West. 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 Portland to Key West round-trip?

    United Airlines, at $384, was found to be the cheapest airline from Portland to Key West.Alternate airlines to your destination round-trip include American Airlines and Delta. United Airlines is priced at 29% lower than the current average price of a flight leaving 3 months from now.

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

    $207 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and American Airlines, with prices starting from $258 and $547, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Key West 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 Portland to Key West?

    Currently, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland to Key West in March is currently the most expensive (average of $493). 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

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 Portland to Key West

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

Top 3 airlines flying from Portland to Key West

Discover the top 3 airlines that operate flights from Portland to Key West. 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$261Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$275Average$564FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$622FlexibilityNo cancel feeOn-time69%

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.