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Florida Keys

$80+ Cheap flights from Oregon to Florida Keys

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Oregon to Florida Keys

Keep the following information in mind while searching for Oregon to Florida Keys flight deals. Data was last updated September 15, 2025.

Round-trip from

$166
(Priceline)

One-way from

$80
(Southwest)

Popular in

December

Cheapest in

August

Average price

$301
From Oregon to Florida Keys
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One-way flight from Oregon to Florida Keys
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Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Oregon to Florida Keys

Cheapest flights from Oregon to Florida Keys
Explore the most affordable flight options available from Oregon to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:26 pmPDX - MIA
1 stop11h 53mFrontier
Sun 11/166:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/13$166
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - MIA
1 stop14h 27mFrontier
Sat 11/86:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/13$176
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2312:43 pmPDX - MIA
1 stop14h 36mFrontier
Sat 11/16:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/13$186
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:26 pmPDX - MIA
2 stops18h 22mFrontier
Mon 11/176:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/14$203
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:43 pmPDX - MIA
2 stops17h 08mFrontier
Sun 10/196:00 amMIA - PDX
1 stop8h 48mFrontier
Deal found 9/14$205
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/155:30 amPDX - MIA
1 stop8h 24mDelta
Tue 10/216:05 pmMIA - PDX
1 stop8h 52mDelta
Deal found 9/13$207
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:03 amPDX - MIA
2 stops17h 16mFrontier
Mon 11/176:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/13$208
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:26 pmPDX - MIA
1 stop11h 53mFrontier
Sun 11/96:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/14$211
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - MIA
1 stop14h 27mFrontier
Thu 11/610:36 pmMIA - PDX
2 stops16h 20mFrontier
Deal found 9/15$212
This CheapOair deal was found by Cheapflights users on 9/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:34 amPDX - MIA
2 stops26h 40mFrontier
Sun 10/196:00 amMIA - PDX
1 stop8h 48mFrontier
Deal found 9/13$218
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/23:26 pmPDX - MIA
1 stop11h 53mFrontier
Wed 11/57:06 pmMIA - PDX
2 stops19h 50mFrontier
Deal found 9/14$219
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 10/225:25 amBOI - MIA
1 stop9h 29mDelta
Sat 10/256:00 amMIA - BOI
1 stop8h 29mDelta
Deal found 9/14$263

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Florida Keys 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 September 15, 2025.
Use the filters below to find and compare flights from Oregon to Florida Keys that are best for you.

Fly from

Oregon

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 11/5

6:00 am-5:30 pm

1 stop8h 30m

Miami

Tue 11/11

6:30 pm-11:58 pm

1 stop8h 28m

$242

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 10/14

9:55 am-10:50 pm

1 stop9h 55m

Miami

Tue 10/21

12:06 pm-7:13 pm

1 stop10h 07m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 10/15

5:30 am-4:54 pm

1 stop8h 24m

Miami

Wed 10/22

7:36 am-4:12 pm

1 stop11h 36m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 10/21

12:40 am-1:28 pm

1 stop9h 48m

Miami

Wed 10/29

7:36 am-4:12 pm

1 stop11h 36m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 10/12

12:40 am-1:28 pm

1 stop9h 48m

Miami

Tue 10/21

2:17 pm-10:08 pm

1 stop10h 51m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 10/27

12:40 am-1:28 pm

1 stop9h 48m

Miami

Tue 11/4

4:35 pm-10:08 pm

1 stop8h 33m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 9/30

7:10 pm-6:25 am

1 stop8h 15m

Miami

Mon 10/6

7:40 am-4:12 pm

1 stop11h 32m

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 9/28

5:15 am-5:23 pm

1 stop9h 08m

Miami

Wed 10/22

6:45 pm-11:43 pm

1 stop7h 58m

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 9/26

6:05 am-5:45 pm

1 stop8h 40m

Miami

Thu 10/2

6:49 pm-12:15 am

1 stop8h 26m

$267

BoiseMiami

BOI - MIA

BOIMIA

Boise Air Term. Gowen Fld

Sat 10/11

5:38 pm-5:29 pm

1 stop21h 51m

Miami

Sat 10/18

6:43 pm-9:35 am

1 stop16h 52m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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 Florida Keys

What is the cheapest month to book a flight from Oregon to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Oregon to Florida Keys (average of $328). Flying from Oregon to Florida Keys in March is currently the most expensive (average of $491). 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 EOA?

Find hourly flight availability from Oregon to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Oregon to Florida Keys. 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 Oregon to Florida Keys?

    Departing from Oregon to Florida Keys will take you 8h 30m. There are 2695 mi between Oregon and Florida Keys. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Oregon to Florida Keys one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $80. Delta flights start at $104 while deals on Frontier start at $114 one-way.

  • Can I find deals for flights from Oregon to Florida Keys that include hotel bookings?

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

  • How can I find direct flights from Oregon to Florida Keys?

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

  • Can I find deals for business class flights from Oregon to Florida Keys?

    Yes. Cheapflights offers flight deals from Oregon to Florida Keys 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 Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Florida Keys (average of $328). Flying from Oregon to Florida Keys in March is currently the most expensive (average of $491). 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

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Alternative routes for Oregon to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Oregon to Florida Keys

Discover the top 3 airlines that operate flights from Oregon to Florida Keys. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$591FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$347Average$740FlexibilityNo cancel feeOn-time69%

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