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Florida Keys

$63+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(Kiwi.com)

One-way from

$63
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$342
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. 10% potential increase in price ($47 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 October 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2812:52 pmPDX - MIA
2 stops20h 37mFrontier
Fri 10/316:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 10/14$202
This Kiwi.com deal was found by Cheapflights users on 10/11. 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.
Sat 11/812:52 pmPDX - MIA
1 stop14h 27mFrontier
Mon 11/178:00 amMIA - PDX
2 stops30h 56mFrontier
Deal found 10/11$208
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:15 amPDX - MIA
Nonstop5h 42mHawaiian Airlines
Wed 12/35:00 pmMIA - PDX
Nonstop6h 50mHawaiian Airlines
Deal found 10/13$209
This Delta deal was found by Cheapflights users on 10/14. 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.
Tue 12/25:30 amPDX - MIA
1 stop8h 20mDelta
Wed 12/102:11 pmMIA - PDX
1 stop8h 24mDelta
Deal found 10/14$217
This Delta deal was found by Cheapflights users on 10/13. 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.
Mon 11/35:30 amPDX - MIA
1 stop8h 24mDelta
Tue 11/116:05 pmMIA - PDX
1 stop9h 09mDelta
Deal found 10/13$218
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/212:40 amPDX - MIA
1 stop9h 48mDelta
Fri 11/77:36 amMIA - PDX
1 stop11h 36mDelta
Deal found 10/13$219
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sat 11/812:52 pmPDX - MIA
1 stop14h 27mFrontier
Thu 11/136:00 amMIA - PDX
2 stops30h 18mFrontier
Deal found 10/12$220
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:55 amPDX - MIA
1 stop7h 05mSouthwest
Tue 11/181:30 pmMIA - PDX
2 stops12h 05mSouthwest
Deal found 10/12$222
This Frontier deal was found by Cheapflights users on 10/13. 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 10/13$224
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 11/41:26 pmPDX - MIA
2 stops20h 03mFrontier
Sat 11/86:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 10/12$227
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Wed 11/267:15 amPDX - MIA
Nonstop5h 42mHawaiian Airlines
Wed 12/35:00 pmMIA - PDX
Nonstop6h 50mHawaiian Airlines
Deal found 10/12$228
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:30 amPDX - EYW
1 stop7h 37mAmerican Airlines
Tue 12/164:10 pmEYW - PDX
1 stop10h 42mAmerican Airlines
Deal found 10/12$389

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 October 14, 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 11/11

7:22 pm-6:25 am

1 stop8h 03m

Miami

Tue 11/18

7:40 am-4:22 pm

1 stop11h 42m

$217

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 11/24

6:29 am-5:33 pm

1 stop8h 04m

Miami

Wed 12/3

7:39 am-4:35 pm

1 stop11h 56m

$218

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 11/3

5:30 am-4:54 pm

1 stop8h 24m

Miami

Fri 11/7

7:36 am-4:12 pm

1 stop11h 36m

$219

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 11/2

5:10 pm-6:21 am

1 stop10h 11m

Miami

Mon 11/10

7:40 am-4:22 pm

1 stop11h 42m

$219

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 12/3

7:18 am-4:00 pm

Nonstop5h 42m

Miami

Tue 12/9

6:34 pm-10:50 am

1 stop19h 16m

$242

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 10/26

12:40 am-1:28 pm

1 stop9h 48m

Miami

Fri 10/31

6:05 pm-11:53 pm

1 stop8h 48m

$267

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 10/20

7:15 pm-6:21 am

1 stop8h 06m

Miami

Wed 10/22

6:05 pm-11:57 pm

1 stop8h 52m

$267

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 11/10

12:35 am-1:32 pm

1 stop9h 57m

Miami

Sun 11/16

7:40 am-4:21 pm

1 stop11h 41m

$268

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 10/25

5:30 am-7:56 pm

2 stops11h 26m

Miami

Thu 10/30

4:11 pm-10:33 pm

1 stop9h 22m

$272

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 12/6

9:10 am-12:46 am

2 stops12h 36m

Miami

Fri 12/12

7:39 am-4:35 pm

1 stop11h 56m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 32 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 $603). 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 October 14, 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
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,079 reviews
Alaska Airlines
8.0
Very good
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
8.0
Very good
7,975 reviews
Alaska Airlines
8.0
Very good
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
8,976 reviews
Alaska Airlines
8.0
Very good
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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
11,042 reviews
Alaska Airlines
8.0
Very good
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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.
Frontier
5.8
Fair
3,135 reviews
Alaska Airlines
8.0
Very good
11,079 reviews

Entertainment

7.0

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.1

Comfort

7.8

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 $242. 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 Alaska Airlines, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Delta and Southwest, 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 $603). 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$610FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$347Average$703FlexibilityNo cancel feeOn-time69%

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