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Florida Keys

$72+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
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 November 10, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$72
(Frontier)

Popular in

December

Cheapest in

September

Average price

$377
Provider with most accurate pricing for Portland-Miami flight deals.
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Provider most trusted by Cheapflights users for Portland-Miami flights.
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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. 11% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 10, 2025.

This American Airlines deal was found by Cheapflights users on 11/8. 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.
Sun 12/710:15 pmPDX - MIA
1 stop7h 48mAmerican Airlines
Tue 12/168:16 pmMIA - PDX
Nonstop6h 36mAmerican Airlines
Deal found 11/8$209
This Delta deal was found by Cheapflights users on 11/9. 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 12/25:30 amPDX - MIA
1 stop8h 20mDelta
Wed 12/106:50 pmMIA - PDX
1 stop8h 14mDelta
Deal found 11/9$217
This Delta deal was found by Cheapflights users on 11/9. 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.
Sat 12/65:25 pmPDX - MIA
1 stop9h 59mDelta
Fri 12/127:39 amMIA - PDX
1 stop11h 56mDelta
Deal found 11/9$218
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:25 pmPDX - MIA
1 stop9h 59mDelta
Sat 12/137:39 amMIA - PDX
1 stop11h 56mDelta
Deal found 11/8$219
This Expedia deal was found by Cheapflights users on 11/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:49 pmPDX - MIA
1 stop20h 45mMultiple Airlines
Sun 12/146:00 amMIA - PDX
1 stop8h 56mMultiple Airlines
Deal found 11/8$232
This Alaska Airlines deal was found by Cheapflights users on 11/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:18 amPDX - MIA
Nonstop5h 42mAlaska Airlines
Tue 12/95:00 pmMIA - PDX
Nonstop6h 50mAlaska Airlines
Deal found 11/9$237
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/75:49 pmPDX - MIA
1 stop20h 45mHawaiian Airlines
Tue 12/165:00 pmMIA - PDX
Nonstop6h 50mHawaiian Airlines
Deal found 11/9$238
This Delta deal was found by Cheapflights users on 11/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:15 pmPDX - MIA
1 stop20h 35mDelta
Mon 12/157:39 amMIA - PDX
1 stop11h 56mDelta
Deal found 11/8$243
This Delta deal was found by Cheapflights users on 11/9. 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.
Thu 12/411:54 amPDX - MIA
1 stop9h 52mDelta
Mon 12/86:05 pmMIA - PDX
1 stop9h 10mDelta
Deal found 11/9$248
This Frontier deal was found by Cheapflights users on 11/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:55 pmPDX - MIA
1 stop13h 24mFrontier
Tue 12/237:05 amMIA - PDX
1 stop9h 19mFrontier
Deal found 11/9$251
This Delta deal was found by Cheapflights users on 11/9. 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.
Thu 11/206:00 amPDX - MIA
1 stop9h 09mDelta
Fri 12/56:50 pmMIA - PDX
1 stop8h 14mDelta
Deal found 11/9$257
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/1710:15 pmPDX - EYW
1 stop10h 53mAmerican Airlines
Fri 12/262:28 pmEYW - PDX
1 stop10h 21mAmerican Airlines
Deal found 11/9$506

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 November 10, 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

Sun 1/25

12:40 am-1:48 pm

1 stop10h 08m

Miami

Fri 1/30

7:50 am-4:30 pm

1 stop11h 40m

$217

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/3

7:11 pm-5:28 am

1 stop7h 17m

Miami

Tue 3/17

8:00 am-4:15 pm

1 stop11h 15m

$217

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 12/2

5:30 am-4:50 pm

1 stop8h 20m

Miami

Wed 12/10

6:50 pm-12:04 am

1 stop8h 14m

$217

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 2/21

6:25 am-5:52 pm

1 stop8h 27m

Miami

Sat 2/28

7:50 am-4:14 pm

1 stop11h 24m

$219

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 12/2

7:18 am-4:00 pm

Nonstop5h 42m

Miami

Wed 12/10

5:00 pm-8:50 pm

Nonstop6h 50m

$237

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 1/27

8:30 am-9:54 pm

2 stops10h 24m

Miami

Thu 1/29

6:20 am-12:18 pm

1 stop8h 58m

$238

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 2/14

6:25 am-5:52 pm

1 stop8h 27m

Miami

Wed 2/18

2:55 pm-8:32 pm

1 stop8h 37m

$248

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 1/6

8:30 am-7:51 pm

1 stop8h 21m

Miami

Mon 1/12

6:20 am-12:18 pm

1 stop8h 58m

$252

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 12/6

2:23 pm-6:24 am

2 stops13h 01m

Miami

Fri 12/12

6:05 pm-12:15 am

1 stop9h 10m

$267

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 2/6

5:23 am-4:37 pm

1 stop8h 14m

Miami

Sat 2/7

6:43 am-12:32 pm

1 stop8h 49m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 37 results
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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, June is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $242). Flying from Portland 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.

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 November 10, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian 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
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,260 reviews
Alaska Airlines
8.0
Very good
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
8,004 reviews
Alaska Airlines
8.0
Very good
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,804 reviews
Alaska Airlines
8.0
Very good
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,012 reviews
Alaska Airlines
8.0
Very good
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,047 reviews
Alaska Airlines
8.0
Very good
11,260 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 5h 42m. Delta provides one of the quickest options available for as low as $237. Portland and Florida Keys are separated by a distance of 2695 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Portland to Florida Keys for a low price.

  • 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, June is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $242). Flying from Portland 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 Portland to Florida Keys

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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 November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$602FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$622FlexibilityNo cancel feeOn-time69%

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