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Florida Keys

$75+ Cheap flights from Portland (PDX) 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Portland to Florida Keys

Keep the following information in mind while searching for Portland to Florida Keys flight deals. Data was last updated September 11, 2025.

Round-trip from

$176
(Frontier)

One-way from

$75
(Southwest)

Popular in

December

Cheapest in

September

Average price

$324
From Portland to Florida Keys
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One-way flight from Portland to Florida Keys
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Highest demand for flights based on searches. 7% potential increase in price ($34 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 Portland to Florida Keys

Cheapest flights from Portland to Florida Keys
Explore the most affordable flight options available from Portland to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Frontier deal was found by Cheapflights users on 9/10. 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.
Sat 11/112:52 pmPDX - MIA
1 stop14h 27mFrontier
Sat 11/86:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/10$176
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:15 amPDX - MIA
1 stop14h 29mFrontier
Sun 10/56:00 amMIA - PDX
1 stop21h 12mFrontier
Deal found 9/10$186
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:40 amPDX - MIA
1 stop9h 48mDelta
Tue 10/146:05 pmMIA - PDX
1 stop8h 52mDelta
Deal found 9/10$197
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:20 amPDX - MIA
1 stop8h 33mDelta
Sat 10/257:36 amMIA - PDX
1 stop11h 36mDelta
Deal found 9/10$202
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2512:43 pmPDX - MIA
2 stops17h 21mMultiple Airlines
Sat 11/16:00 amMIA - PDX
1 stop8h 56mMultiple Airlines
Deal found 9/10$204
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:43 pmPDX - MIA
2 stops20h 38mMultiple Airlines
Fri 10/316:00 amMIA - PDX
1 stop8h 56mMultiple Airlines
Deal found 9/10$206
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 9/307:10 pmPDX - MIA
1 stop8h 15mDelta
Mon 10/67:40 amMIA - PDX
1 stop11h 32mDelta
Deal found 9/11$207
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier 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
Mon 11/176:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/11$208
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/2412:43 pmPDX - MIA
1 stop24h 31mFrontier
Fri 10/316:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 9/9$209
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:43 pmPDX - MIA
1 stop24h 31mMultiple Airlines
Sun 10/266:16 pmMIA - PDX
2 stops20h 32mMultiple Airlines
Deal found 9/10$211
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/15:15 amPDX - MIA
1 stop9h 08mDelta
Sat 10/47:43 amMIA - PDX
1 stop11h 19mDelta
Deal found 9/9$212
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/49:56 pmPDX - EYW
1 stop11h 09mAmerican Airlines
Fri 10/102:32 pmEYW - PDX
1 stop10h 04mAmerican Airlines
Deal found 9/8$329

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 11, 2025.
Use the filters below to find and compare flights from Portland to Florida Keys that are best for you.

Fly from

Portland

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 2/24

6:15 am-5:43 pm

1 stop8h 28m

Miami

Wed 3/4

8:00 am-4:15 pm

1 stop11h 15m

$197

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 10/7

12:40 am-1:28 pm

1 stop9h 48m

Miami

Wed 10/15

7:36 am-4:12 pm

1 stop11h 36m

$207

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 10/27

10:10 pm-11:08 am

1 stop9h 58m

Miami

Fri 10/31

6:05 pm-11:53 pm

1 stop8h 48m

$207

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 1/4

6:27 pm-5:53 am

1 stop8h 26m

Miami

Thu 1/8

6:20 am-12:18 pm

1 stop8h 58m

$242

PortlandMiami

PDX - MIA

PDXMIA

Portland

Thu 10/2

7:05 pm-6:25 am

1 stop8h 20m

Miami

Mon 10/6

7:40 am-4:12 pm

1 stop11h 32m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 10/25

12:40 am-1:28 pm

1 stop9h 48m

Miami

Tue 10/28

11:16 am-9:04 pm

1 stop12h 48m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 1/6

7:00 am-3:51 pm

Nonstop5h 51m

Miami

Thu 1/15

4:45 pm-8:23 pm

Nonstop6h 38m

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 9/26

7:15 am-9:14 pm

1 stop10h 59m

Miami

Thu 10/2

7:43 am-4:02 pm

1 stop11h 19m

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 9/24

5:15 am-5:23 pm

1 stop9h 08m

Miami

Sat 9/27

7:43 am-4:02 pm

1 stop11h 19m

$267

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 10/4

2:56 pm-10:54 am

2 stops16h 58m

Key West

Fri 10/10

2:32 pm-9:36 pm

1 stop10h 04m

$388

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 28 results
1
2
3

Best time to book a flight from Portland to Florida Keys

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

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

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

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United Airlines from Portland to Florida Keys by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,177 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Comfort

7.8

Food

7.1

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

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

    Located just 6.0 mi from the city center, Portland (PDX) is the airport most travelers will use when flying to Florida Keys from Portland.

  • How long is the flight from Portland to Florida Keys?

    A quick flight from Portland to Florida Keys can take about 8h 26m. Delta provides one of the quickest options available for as low as $242. Portland and Florida Keys are separated by a distance of 2695 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

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

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Alternative routes for Portland 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 Portland to Florida Keys

Discover the top 3 airlines that operate flights from Portland 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$610FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$588FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$622FlexibilityNo cancel feeOn-time69%

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