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Florida Keys

$88+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap 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 February 13, 2026.

This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/111:56 am
BOI
-
MIA
1 stop15h 18m
Frontier
Sat 3/78:08 pm
MIA
-
BOI
1 stop16h 12m
Frontier
Deal found 2/10$210
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Sun 5/1012:52 pm
PDX
-
MIA
1 stop15h 40m
Frontier
Sat 5/168:42 am
MIA
-
PDX
1 stop27h 17m
Frontier
Deal found 2/13$211
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:52 pm
PDX
-
MIA
1 stop15h 40m
Frontier
Sat 4/256:30 am
MIA
-
PDX
1 stop31h 33m
Frontier
Deal found 2/11$213
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:48 am
PDX
-
MIA
1 stop14h 17m
Frontier
Sun 4/195:05 am
MIA
-
PDX
2 stops32h 58m
Frontier
Deal found 2/12$214
This Delta deal was found by Cheapflights users on 2/13. 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.
Tue 4/712:30 am
PDX
-
MIA
1 stop10h 06m
Delta
Wed 4/157:10 am
MIA
-
PDX
1 stop11h 28m
Delta
Deal found 2/13$215
This eDestinos deal was found by Cheapflights users on 2/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:52 pm
PDX
-
MIA
1 stop15h 40m
Frontier
Sun 4/268:42 am
MIA
-
PDX
1 stop27h 17m
Frontier
Deal found 2/12$217
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:52 pm
PDX
-
MIA
1 stop15h 40m
Frontier
Tue 4/217:50 am
MIA
-
PDX
1 stop32h 12m
Frontier
Deal found 2/12$218
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:52 pm
PDX
-
MIA
1 stop15h 40m
Frontier
Wed 4/297:50 am
MIA
-
PDX
1 stop30h 13m
Frontier
Deal found 2/12$219
This Frontier deal was found by Cheapflights users on 2/13. 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.
Wed 5/61:48 pm
PDX
-
MIA
1 stop12h 17m
Frontier
Mon 5/115:50 am
MIA
-
PDX
1 stop8h 13m
Frontier
Deal found 2/13$221
This Frontier deal was found by Cheapflights users on 2/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:48 am
PDX
-
MIA
1 stop14h 17m
Frontier
Thu 5/75:50 am
MIA
-
PDX
1 stop8h 13m
Frontier
Deal found 2/12$222
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/812:15 pm
BOI
-
MIA
1 stop15h 23m
Frontier
Wed 3/185:50 am
MIA
-
BOI
1 stop31h 30m
Frontier
Deal found 2/9$222
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/85:40 pm
PDX
-
MIA
1 stop10h 09m
Delta
Tue 3/175:56 pm
MIA
-
PDX
1 stop9h 03m
Delta
Deal found 2/12$224

Find 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 February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(Kiwi.com)

One-way from

$88
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$387
Provider with most accurate pricing for Portland-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Miami flights.
Search Deals
From Oregon to Florida Keys
Search Deals
One-way flight from Oregon to Florida Keys
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 13, 2026.
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

Sun 3/15

5:40 pm-6:49 am

1 stop10h 09m

Miami

Thu 3/19

6:55 am-12:35 pm

1 stop8h 40m

$224

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/3

5:30 am-5:24 pm

1 stop8h 54m

Miami

Tue 4/7

5:56 pm-11:59 pm

1 stop9h 03m

$225

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 3/16

7:15 pm-5:40 am

1 stop7h 25m

Miami

Thu 3/19

1:13 pm-7:00 pm

1 stop8h 47m

$234

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/3

7:00 am-3:44 pm

Nonstop5h 44m

Miami

Tue 4/7

4:44 pm-8:35 pm

Nonstop6h 51m

$237

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/17

5:40 pm-6:49 am

1 stop10h 09m

Miami

Tue 3/24

5:56 pm-11:59 pm

1 stop9h 03m

$237

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 5/16

5:18 pm-6:45 am

1 stop10h 27m

Miami

Sat 5/23

8:00 am-4:23 pm

1 stop11h 23m

$256

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/3

1:18 pm-11:33 pm

1 stop7h 15m

Miami

Wed 3/4

8:45 am-6:55 pm

2 stops13h 10m

$262

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/3

9:45 pm-9:26 am

1 stop8h 41m

Miami

Thu 3/5

7:50 am-4:10 pm

1 stop11h 20m

$265

RedmondMiami

RDM - MIA

RDMMIA

Bend/Redmond

Mon 3/30

5:50 am-5:04 pm

1 stop8h 14m

Miami

Tue 4/7

6:04 pm-12:29 pm

1 stop21h 25m

$283

RedmondMiami

RDM - MIA

RDMMIA

Bend/Redmond

Mon 3/30

5:50 am-5:04 pm

1 stop8h 14m

Miami

Wed 4/8

6:04 pm-8:57 am

1 stop17h 53m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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, June is the cheapest month in which you can book a flight from Oregon to Florida Keys (average of $242). Flying from Oregon to Florida Keys in October is currently the most expensive (average of $715). 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.

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 5h 44m. 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 American Airlines, which is currently one of the cheapest options available, starting at $100. Frontier flights start at $103 while deals on Delta start at $109 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, June is the cheapest month in which you can book a flight from Oregon to Florida Keys (average of $242). Flying from Oregon to Florida Keys in October is currently the most expensive (average of $715). 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

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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 February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$581FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$611FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$648Average$753FlexibilityNo cancel feeOn-time69%

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