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Florida Keys

$52+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$205
(Kiwi.com)

One-way from

$52
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$332
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 ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/412:51 pmPDX - MIA
1 stop13h 28mMultiple Airlines
Thu 12/116:05 amMIA - PDX
2 stops32h 51mMultiple Airlines
Deal found 10/28$205
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/412:51 pmPDX - MIA
1 stop13h 28mFrontier
Wed 12/106:00 amMIA - PDX
2 stops37h 37mFrontier
Deal found 10/28$209
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/412:51 pmPDX - MIA
1 stop13h 28mMultiple Airlines
Sat 12/139:59 pmMIA - PDX
2 stops16h 57mMultiple Airlines
Deal found 10/29$212
This Expedia deal was found by Cheapflights users on 10/28. 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.
Sat 11/1512:52 pmPDX - MIA
1 stop14h 27mMultiple Airlines
Wed 11/196:46 pmMIA - PDX
1 stop8h 23mMultiple Airlines
Deal found 10/28$214
This Delta deal was found by Cheapflights users on 10/28. 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
Thu 12/46:50 pmMIA - PDX
1 stop8h 14mDelta
Deal found 10/28$217
This Delta deal was found by Cheapflights users on 10/28. 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 12/45:30 amPDX - MIA
1 stop8h 20mDelta
Sat 12/611:30 amMIA - PDX
1 stop12h 10mDelta
Deal found 10/28$218
This Delta deal was found by Cheapflights users on 10/28. 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 10/28$219
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/412:51 pmPDX - MIA
1 stop13h 28mMultiple Airlines
Sun 12/76:05 amMIA - PDX
2 stops15h 26mMultiple Airlines
Deal found 10/28$221
This Frontier deal was found by Cheapflights users on 10/27. 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 11/1312:52 pmPDX - MIA
1 stop14h 27mFrontier
Mon 11/176:00 amMIA - PDX
1 stop8h 56mFrontier
Deal found 10/27$226
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/610:45 pmPDX - MIA
Nonstop5h 34mAmerican Airlines
Fri 12/128:16 pmMIA - PDX
Nonstop6h 36mAmerican Airlines
Deal found 10/30$237
This Frontier deal was found by Cheapflights users on 10/28. 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 11/1512:52 pmPDX - MIA
1 stop14h 27mFrontier
Sun 11/236:15 amMIA - PDX
1 stop11h 52mFrontier
Deal found 10/28$243
This Delta deal was found by Cheapflights users on 10/30. 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 11/285:30 amPDX - EYW
2 stops11h 23mDelta
Mon 12/87:40 amEYW - PDX
2 stops16h 12mDelta
Deal found 10/30$589

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 30, 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 12/9

11:20 pm-11:03 am

1 stop8h 43m

Miami

Fri 12/12

7:39 am-4:35 pm

1 stop11h 56m

$218

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 12/6

11:54 am-12:46 am

1 stop9h 52m

Miami

Fri 12/12

7:39 am-4:35 pm

1 stop11h 56m

$219

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 11/10

8:45 pm-5:46 pm

1 stop18h 01m

Miami

Tue 11/18

6:46 pm-12:09 am

1 stop8h 23m

$246

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

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 11/10

5:30 am-4:49 pm

1 stop8h 19m

Miami

Tue 11/18

4:52 pm-10:21 pm

1 stop8h 29m

$257

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 1/6

6:14 am-5:11 pm

1 stop7h 57m

Miami

Thu 1/29

4:39 pm-8:27 pm

Nonstop6h 48m

$267

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 1/19

12:40 am-1:48 pm

1 stop10h 08m

Miami

Mon 1/26

5:47 pm-12:17 am

1 stop9h 30m

$277

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 12/9

5:30 am-4:50 pm

1 stop8h 20m

Miami

Fri 12/19

6:05 pm-12:15 am

1 stop9h 10m

$277

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 11/9

11:59 pm-11:49 am

1 stop8h 50m

Miami

Thu 11/13

8:45 am-2:46 pm

1 stop9h 01m

$297

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 12/3

7:18 am-4:00 pm

Nonstop5h 42m

Miami

Sat 12/6

5:00 pm-8:50 pm

Nonstop6h 50m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 26 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, 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 30, 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
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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
11,217 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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
7,998 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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
8,998 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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
11,035 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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
3,122 reviews
Alaska Airlines
8.0
Very good
11,217 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Comfort

7.8

Entertainment

7.0

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 8h 43m. Delta provides one of the quickest options available for as low as $218. 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 Delta, with whom users have recently found tickets for as low as $109. However, be on the lookout for offers from American Airlines and United 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 $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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$610FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$703FlexibilityNo cancel feeOn-time69%

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