HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$207+ Cheap flights from Oregon to Key West (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 Oregon 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.

Cheap flight deals from Oregon to Key West

Keep the following information in mind while searching for Oregon to Key West flight deals. Data was 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 Oregon to Key West
Search Deals
One-way flight from Oregon 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 Oregon to Key West

Cheapest flights from Oregon to Key West
Explore the most affordable flight options available from Oregon 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 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 6/2011:40 pmBOI - EYW
1 stop9h 13mDelta
Tue 6/242:05 pmEYW - BOI
1 stop10h 24mDelta
Deal found 6/11$719
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 6/206:52 amBOI - EYW
2 stops10h 10mAmerican Airlines
Tue 6/2411:20 amEYW - BOI
2 stops12h 45mAmerican Airlines
Deal found 6/11$741
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/274:40 pmBOI - EYW
2 stops19h 20mUnited Airlines
Tue 7/12:12 pmEYW - BOI
3 stops23h 31mUnited Airlines
Deal found 6/12$846
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 Oregon 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 Oregon to Key West that are best for you.

Fly from

Oregon

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

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 6/27

6:52 am-7:02 pm

2 stops10h 10m

Key West

Tue 7/1

11:20 am-11:36 pm

2 stops14h 16m

$762

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 6/27

11:40 pm-10:53 am

1 stop9h 13m

Key West

Tue 7/1

2:05 pm-10:29 pm

1 stop10h 24m

$819

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 6/27

4:40 pm-2:00 pm

2 stops19h 20m

Key West

Tue 7/1

2:12 pm-11:43 am

3 stops23h 31m

$846

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 11 results
1
2

Best time to book a flight from Oregon to Key West

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

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

Currently, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon 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.

What is the cheapest time of day to fly from OR to EYW?

Find hourly flight availability from Oregon to Key West. 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.

When flying from Oregon to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.
To help decide which airline to fly from Oregon to Key West, see what other customers have to say about Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

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

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

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
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

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

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

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

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

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 Oregon 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 airport do you fly into for flights to Key West from Oregon?

    Located just 2.6 mi from the city center, Key West (EYW) is the airport most travelers will use when flying to Key West from Oregon.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $207. Users have also found prices from $258 and $547 on Delta and American Airlines, respectively.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon 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 Oregon to Key West

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
LaGuardia to Miami flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Orlando flights
Los Angeles to Miami flights
Los Angeles to Orlando flights
Dallas/Fort Worth to Miami flights
John F Kennedy Intl to West Palm Beach flights
Philadelphia to Orlando flights
Baltimore to Fort Lauderdale flights
Baltimore to Miami flights
Dallas/Fort Worth to Orlando flights
O'Hare Intl to Orlando flights
Atlanta to Miami flights
Dulles Intl to Miami flights
Los Angeles to Fort Lauderdale flights
Dallas/Fort Worth to Fort Lauderdale flights
O'Hare Intl to Fort Lauderdale flights
John F Kennedy Intl to Tampa flights
Newark to Tampa flights
Boston to Orlando flights
Reagan-National to Miami flights
Dulles Intl to Orlando flights
Reagan-National to Orlando flights
O'Hare Intl to Miami flights
Philadelphia to Fort Lauderdale flights
Hobby to Miami flights
Atlanta to Fort Lauderdale flights
Philadelphia to Miami flights
Boston to Miami flights
Boston to Fort Lauderdale flights
Baltimore to Orlando flights
LaGuardia to West Palm Beach flights
LaGuardia to Tampa flights
Dulles Intl to Fort Lauderdale flights
Denver to Orlando flights
Providence to Orlando flights
Hobby to Orlando flights
Raleigh to Miami flights
Cleveland to Orlando flights
San Francisco to Miami flights
Newark to West Palm Beach flights
O'Hare Intl to Tampa flights
Islip to Orlando flights
George Bush Intcntl to Orlando flights

Top 3 airlines flying from Oregon to Key West

Discover the top 3 airlines that operate flights from Oregon 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$647FlexibilityNo 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.