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Florida Keys

$105+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$213
(American Airlines)

One-way from

$105
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$369
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. 9% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/7. 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 2/1511:35 pmPDX - MIA
1 stop8h 40mAmerican Airlines
Wed 2/188:05 pmMIA - PDX
Nonstop6h 45mAmerican Airlines
Deal found 1/7$213
This Delta deal was found by Cheapflights users on 1/8. 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.
Wed 2/45:08 pmPDX - MIA
1 stop9h 20mDelta
Wed 2/186:29 pmMIA - PDX
1 stop8h 46mDelta
Deal found 1/8$215
This Delta deal was found by Cheapflights users on 1/6. 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 2/15:25 pmPDX - MIA
1 stop10h 10mDelta
Wed 2/47:50 amMIA - PDX
1 stop11h 35mDelta
Deal found 1/6$216
This Delta deal was found by Cheapflights users on 1/7. 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.
Fri 1/305:25 pmPDX - MIA
1 stop10h 15mDelta
Sat 2/77:52 amMIA - PDX
1 stop11h 35mDelta
Deal found 1/7$217
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Fri 2/610:15 pmPDX - MIA
1 stop8h 57mAmerican Airlines
Sat 2/147:07 amMIA - PDX
1 stop9h 47mAmerican Airlines
Deal found 1/7$219
This Southwest deal was found by Cheapflights users on 1/7. 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 3/36:30 amPDX - MIA
2 stops11h 30mSouthwest
Thu 3/126:05 pmMIA - PDX
1 stop9h 40mSouthwest
Deal found 1/7$225
This American Airlines deal was found by Cheapflights users on 1/5. 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 10/242:12 pmPDX - MIA
1 stop7h 40mAmerican Airlines
Sun 11/18:19 pmMIA - PDX
Nonstop6h 32mAmerican Airlines
Deal found 1/5$229
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Tue 1/2711:01 pmPDX - MIA
Nonstop5h 33mAmerican Airlines
Fri 1/307:55 pmMIA - PDX
Nonstop6h 51mAmerican Airlines
Deal found 1/7$230
This United Airlines deal was found by Cheapflights users on 1/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/297:00 amPDX - MIA
1 stop8h 25mUnited Airlines
Mon 2/26:20 amMIA - PDX
1 stop8h 58mUnited Airlines
Deal found 1/7$233
This Southwest deal was found by Cheapflights users on 1/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/276:20 amPDX - MIA
2 stops11h 40mSouthwest
Tue 2/312:55 pmMIA - PDX
2 stops12h 20mSouthwest
Deal found 1/8$234
This Delta deal was found by Cheapflights users on 1/6. 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 1/271:30 pmPDX - MIA
2 stops12h 58mDelta
Thu 2/511:39 amMIA - PDX
1 stop11h 46mDelta
Deal found 1/6$235
This United Airlines deal was found by Cheapflights users on 1/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:50 pmPDX - EYW
1 stop10h 33mUnited Airlines
Wed 3/112:24 pmEYW - PDX
1 stop10h 28mUnited Airlines
Deal found 1/5$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 January 8, 2026.
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 1/27

9:45 pm-10:40 am

1 stop9h 55m

Miami

Fri 2/6

7:50 am-4:25 pm

1 stop11h 35m

$216

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 2/4

7:10 am-12:51 am

2 stops14h 41m

Miami

Wed 2/18

6:29 pm-12:15 am

1 stop8h 46m

$251

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 2/24

1:27 pm-5:28 am

2 stops13h 01m

Miami

Wed 3/4

6:39 pm-12:15 am

1 stop8h 36m

$251

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 2/4

11:59 am-12:51 am

1 stop9h 52m

Miami

Sat 2/7

7:52 am-6:50 pm

2 stops13h 58m

$255

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 1/18

5:25 pm-6:35 am

1 stop10h 10m

Miami

Fri 1/30

7:50 am-4:25 pm

1 stop11h 35m

$256

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 1/20

6:30 am-9:30 pm

1 stop12h 00m

Miami

Tue 1/27

12:55 pm-10:15 pm

2 stops12h 20m

$271

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 2/6

11:05 pm-2:38 pm

1 stop12h 33m

Miami

Mon 2/9

6:20 am-12:18 pm

1 stop8h 58m

$291

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 1/14

7:00 am-8:26 pm

1 stop10h 26m

Miami

Wed 1/21

7:50 am-4:25 pm

1 stop11h 35m

$295

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 1/18

5:25 pm-6:35 am

1 stop10h 10m

Miami

Fri 1/23

4:44 pm-10:45 pm

1 stop9h 01m

$295

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 1/18

5:25 pm-6:35 am

1 stop10h 10m

Miami

Wed 1/21

11:39 am-8:25 pm

1 stop11h 46m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 34 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 January 8, 2026.
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
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,661 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,025 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Hawaiian Airlines
7.8
Good
2,824 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,139 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
American Airlines
7.2
Good
11,095 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Crew

8.5

Comfort

7.8

Boarding

8.1

Food

7.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

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 9h 20m. Delta provides one of the quickest options available for as low as $329. Portland and Florida Keys are separated by a distance of 2685 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 $88. However, be on the lookout for offers from American Airlines and Delta, 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.

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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 2 airlines flying from Portland to Florida Keys

Discover the top 2 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$591FlexibilityNo cancel feeOn-time71%

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