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Cheap flights from Oregon to Key West from $367

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Key West departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Oregon to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:44 pm - 11:02 am
PDX
-
EYW
17h 18m
1 stop
Multiple Airlines Logo
11:46 am - 10:20 am
EYW
-
PDX
25h 34m
2 stops
$367Multiple Airlines
Thu, May 28 - Wed, Jun 3
Delta Logo
9:39 pm - 10:53 am
PDX
-
EYW
10h 14m
1 stop
Delta Logo
7:30 am - 7:23 pm
EYW
-
PDX
14h 53m
2 stops
$394Delta
Sat, May 16 - Wed, May 20
American Airlines Logo
5:49 am - 6:47 pm
PDX
-
EYW
9h 58m
1 stop
American Airlines Logo
4:40 pm - 11:53 pm
EYW
-
PDX
10h 13m
1 stop
$409American Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
5:20 am - 6:47 pm
PDX
-
EYW
10h 27m
2 stops
American Airlines Logo
4:40 pm - 11:53 pm
EYW
-
PDX
10h 13m
1 stop
$414American Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
11:40 pm - 1:21 pm
PDX
-
EYW
10h 41m
2 stops
American Airlines Logo
2:01 pm - 10:47 pm
EYW
-
PDX
11h 46m
2 stops
$419American Airlines
Sat, May 16 - Wed, May 20
Delta Logo
6:00 am - 7:53 pm
PDX
-
EYW
10h 53m
2 stops
Delta Logo
11:56 am - 10:13 pm
EYW
-
PDX
13h 17m
2 stops
$420Delta
Sat, Jul 4 - Thu, Jul 9
Delta Logo
11:12 pm - 1:00 pm
PDX
-
EYW
10h 48m
2 stops
Delta Logo
2:00 pm - 10:02 pm
EYW
-
PDX
11h 02m
2 stops
$429Delta
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:49 am - 6:49 pm
PDX
-
EYW
10h 00m
1 stop
American Airlines Logo
1:39 pm - 11:52 pm
EYW
-
PDX
13h 13m
2 stops
$434American Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
10:59 pm - 4:07 pm
PDX
-
EYW
14h 08m
2 stops
American Airlines Logo
1:39 pm - 11:59 pm
EYW
-
PDX
13h 20m
2 stops
$439American Airlines
Thu, May 28 - Wed, Jun 3
American Airlines Logo
11:23 pm - 11:16 am
PDX
-
EYW
8h 53m
1 stop
American Airlines Logo
3:58 pm - 11:53 pm
EYW
-
PDX
10h 55m
1 stop
$449American Airlines
Tue, May 5 - Sat, May 9

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United Airlines flights from Oregon to Key West

Our best United Airlines deals on Oregon to Key West flight tickets
United Airlines
Aug 29
BOI7:05 amBoise Air Term. Gowen Fld
13h 06m
2 stops
EYW10:11 pmKey West
Sep 2
EYW2:20 pmKey West
31h 07m
2 stops
BOI7:27 pmBoise Air Term. Gowen Fld
$931
United Airlines
Aug 29
BOI12:23 pmBoise Air Term. Gowen Fld
7h 48m
1 stop
EYW10:11 pmKey West
Sep 2
EYW2:20 pmKey West
31h 07m
2 stops
BOI7:27 pmBoise Air Term. Gowen Fld
$973

American Airlines flights from Oregon to Key West

Our best American Airlines deals on Oregon to Key West flight tickets
American Airlines
Jul 14
PDX5:49 amPortland
9h 58m
1 stop
EYW6:47 pmKey West
Jul 21
EYW4:40 pmKey West
10h 13m
1 stop
PDX11:53 pmPortland
$409
American Airlines
Jul 14
PDX5:20 amPortland
10h 27m
2 stops
EYW6:47 pmKey West
Jul 21
EYW4:40 pmKey West
10h 13m
1 stop
PDX11:53 pmPortland
$414
American Airlines
May 16
PDX11:40 pmPortland
10h 41m
2 stops
EYW1:21 pmKey West
May 20
EYW2:01 pmKey West
11h 46m
2 stops
PDX10:47 pmPortland
$419

momondo 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, momondo users made 832,500 searches. Data last updated April 24, 2026.
Use the filters below to find and compare flights from Oregon to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 5/28

2:44 pm-11:02 am

1 stop17h 18m

Key West

Wed 6/3

11:46 am-10:20 am

2 stops25h 34m

$367

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 5/16

9:39 pm-10:53 am

1 stop10h 14m

Key West

Wed 5/20

7:30 am-7:23 pm

2 stops14h 53m

$394

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/14

5:49 am-6:47 pm

1 stop9h 58m

Key West

Tue 7/21

4:40 pm-11:53 pm

1 stop10h 13m

$409

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/14

5:20 am-6:47 pm

2 stops10h 27m

Key West

Tue 7/21

4:40 pm-11:53 pm

1 stop10h 13m

$414

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 5/16

11:40 pm-1:21 pm

2 stops10h 41m

Key West

Wed 5/20

2:01 pm-10:47 pm

2 stops11h 46m

$419

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 7/4

6:00 am-7:53 pm

2 stops10h 53m

Key West

Thu 7/9

11:56 am-10:13 pm

2 stops13h 17m

$420

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 5/28

11:12 pm-1:00 pm

2 stops10h 48m

Key West

Tue 6/2

2:00 pm-10:02 pm

2 stops11h 02m

$429

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 5/27

5:49 am-6:49 pm

1 stop10h 00m

Key West

Tue 6/2

1:39 pm-11:52 pm

2 stops13h 13m

$434

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 5/28

10:59 pm-4:07 pm

2 stops14h 08m

Key West

Wed 6/3

1:39 pm-11:59 pm

2 stops13h 20m

$439
Quickest round-trip

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 5/5

11:23 pm-11:16 am

1 stop8h 53m

Key West

Sat 5/9

3:58 pm-11:53 pm

1 stop10h 55m

$449

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Key West from

How to get the cheapest flight ticket from Oregon to Key West

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Key West?

In general, April is the cheapest month to fly from Oregon to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $425. If you are unable to visit Key West during the month of April, then departing from Oregon during the month December is also very affordable. Most momondo users find prices during this month for around $466.

Can stopping save me money on Oregon to Key West flights?

You could potentially save up to 52% on your flight if you consider stops on a Oregon to Key West flight.

Cheap Oregon to Key West flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oregon to Key West

Fastest flight time

8h 07m

Direct flights

None
The fastest flight from Oregon to Key West takes 8h 07m
There are no direct flights from Oregon to Key West. There are no popular flight routes from Oregon to Key West.
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Frequently asked questions about flying from Oregon to Key West

  • When did momondo last update prices for flights from Oregon to Key West Airport?

    Prices for flights from Oregon to Key West Airport were last updated today.

  • How many operators does momondo search for flights from Oregon to Key West Airport?

  • How old do you have to be to fly from Oregon to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents required for your trip to Key West Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Key West Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Oregon to Key West

Compare and see reviews for airlines that fly from Oregon to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $242Free CancellationRating
7.9
8,450 reviews
Search Delta flights
American AirlinesPriceFrom $314Free CancellationRating
7.1
11,666 reviews
Search American Airlines flights
United AirlinesPriceFrom $648Free CancellationRating
7.4
9,643 reviews
Search United Airlines flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

Why should I use momondo to find a flight deal from Oregon to Key West?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oregon to Key West. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Oregon to Key West with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Oregon to Key West flights to just show those with flexible booking policies.

How can momondo help me find flights from Oregon to Key West?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oregon to Key West.

I’m not ready to book a flight from Oregon to Key West right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Key West from Oregon. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Key West trip

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